- Ionic Liquid-Based Microemulsions in Catalysis
-
The design and properties of surface-active ionic liquids that are able to form stable microemulsions with heptane and water are presented, and their promise as reaction media for thermomorphic palladium-catalyzed cross-coupling reactions is demonstrated.
- Hejazifar, Mahtab,Earle, Martyn,Seddon, Kenneth R.,Weber, Stefan,Zirbs, Ronald,Bica, Katharina
-
-
Read Online
- Palladium(II) complexes bearing N-alkylpiperidoimidazolin-2-ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity
-
A series of piperidoimidazolinium salts which differ in the chain lengths (butyl, octyl, dodecyl, octadecyl) and their Pd–N-heterocyclic carbene complexes with pyridine were synthesized and characterized using elemental analysis and spectroscopic methods. The effects of these ligands on catalyst activation and the performance of the complexes were studied in Suzuki–Miyaura reactions of arylboronic acid with aryl chlorides. The complex with the ligand having the longest chain length was found to be most active. The results demonstrated that the length of the alkyl chain of the piperidoimidazolin-2-ylidene controlled the dispersion and composition of the nanoparticles and it affected the catalytic activity. The impact of alkyl chain length of piperidoimidazolin-2-ylidene on the Suzuki–Miyaura reactions of arylboronic acid with aryl halides was systematically investigated.
- ?ak?r, Sinem,Türkmen, Gül?ah,Türkmen, Hayati
-
-
Read Online
- Iron-catalyzed Suzuki-Miyaura cross-coupling reaction
-
An efficient, mild, and simple protocol for iron-catalyzed Suzuki-Miyaura type cross-coupling reaction between iodo- or bromoaryl derivatives and arylboronic acids was developed. In the presence of iron(III) chloride (10 mol%) and a stoichiometric amount of potassium fluoride, aryl iodides and bromides reacted with arylboronic acids in ethanol at 100 °C under air to give the corresponding bis-aryl compounds with good to excellent yields.
- Bezier, David,Darcel, Christophe
-
-
Read Online
- Amine-bridged bis(phenol) ligands for efficient Pd-catalyzed aqueous C-C coupling reactions
-
The influence of ring size (5 or 6), chain length (1, 2 or 3) and bulkiness of N-aryl substituents in amine-bridged bis(phenol) ligands (1, 2, 3) on palladium-catalyzed aqueous C-C coupling reactions were revealed. The homocoupling of arylboronic acid can be completed in neat water with the aid of a catalytic amount of p-toluenesulfonyl chloride (TsCl) in a very short time under anaerobic or aerobic conditions. Interestingly, the same catalytic system was efficient for Suzuki-Miyaura reaction in aqueous acetone under aerobic conditions in the absence of TsCl. The crystal structures of ligand 1 and three unsymmetrical fluorine-substituted biaryl derivatives were also reported. Copyright
- Zhou, Zhonggao,Liu, Minyan,Wu, Xiaoli,Yu, Hongwei,Xu, Guohai,Xie, Yongrong
-
-
Read Online
- Synthesis of chiral imidazolium salts from a carbohydrate and their application in Pd-catalyzed Suzuki-Miyaura reaction
-
A series of chiral 1-(acetylated glucopyranosyl)-3-substituted-imidazolium salts [3-substitute = nbutyl (1a), 3-bromopropyl (1b), 2-chloromethyl benzyl (1c), and 4-chloromethyl benzyl (1d)] have been synthesized. Preliminary catalytic studies show that these imidazolinium salts are remarkably efficient in Pd-catalyzed Suzuki-Miyaura reaction. Functionalized aryl boronic acids reaction with aryl halides (including aryl iodides, aryl bromides and activated aryl chlorides) using environmentally friendly conditions (ethanol aqueous and ambient). The excellent isolate yields reveal that the bulky carbohydrate unit is promising for the construction of highly active transition-metal catalyst.
- Zhou, Zhonggao,Qiu, Jiabin,Xie, Lifang,Du, Fan,Xu, Guohai,Xie, Yongrong,Ling, Qidan
-
-
Read Online
- Immobilization of dipyridyl complex to magnetic nanoparticle via click chemistry as a recyclable catalyst for Suzuki cross-coupling reactions
-
A magnetic nanoparticle (MNP)-supported di(2-pyridyl)methanol palladium dichloride complex was prepared via click chemistry. The MNP-supported catalyst was evaluated in Suzuki coupling reaction in term of activity and recyclability in DMF. It was found to be highly efficient for Suzuki coupling reaction using aryl bromides as substrates and could be easily separated by an external magnet and reused in five consecutive runs without obvious loss of activity. Georg Thieme Verlag Stuttgart.
- Lv, Guanghua,Mai, Wenpeng,Jin, Rizhe,Gao, Lianxun
-
-
Read Online
- PEG-supported dipyridyl ligand for palladium-catalyzed Suzuki and Suzuki-type reactions in PEG and aqueous media
-
An air- and water-stable PEG-supported bidentate nitrogen ligand is prepared and its applications in the palladium-catalyzed Suzuki reaction of aryl halides with arylboronic acids in PEG and Suzuki-type reaction of aryl halides with sodium tetraphenylborate in aqueous media are reported. The homogeneous catalyst system is environmentally friendly and offers the advantages of high activity, reusability and easy separation. Georg Thieme Verlag Stuttgart.
- Mai, Wenpeng,Gao, Lianxun
-
-
Read Online
- PEG-functionalized NHC ligands for efficient and recyclable palladium-catalyzed Suzuki reactions in water
-
We have used poly(ethylene glycol)-functionalized N-heterocyclic carbene ligands, 1-(methoxy PEG)-3-methylimidazolium iodides together with Pd(OAc) 2 as efficient catalysts for the Suzuki reaction in water. The best catalytic system generated in situ from Pd(OAc)2, mPEG 16MeImI, and K2CO3 is able to mediate the Suzuki coupling of a series of aryl boronic acids and aryl halides, except for deactivated aryl chlorides, in good to almost quantitative yields in water within 6 h. After extraction of the product, the catalyst containing mPEG n MeImI phase could be recycled for five times without significant loss of activity. Graphical Abstract: Three PEG-modified NHC ligands with different PEG chain lengths (mPEGnMeImI, n = 7, 12, and 16) were used for Pd-catalyzed Suzuki reactions in water. The best catalytic system generated in situ from Pd(OAc)2, mPEG16MeImI, and K 2CO3 is able to mediate the Suzuki coupling of a series of aryl boronic acids and aryl halides, except for deactivated aryl chlorides, in good to almost quantitative yields in water within 6 h. After extraction of the product, the catalyst containing mPEGn MeImI phase could be recycled for five times without significant loss of activity.
- Xue, Jun,Zhou, Zhonggao,Peng, Jie,Du, Fan,Xie, Lifang,Xu, Guohai,Huang, Guiping,Xie, Yongrong
-
-
Read Online
- Complexes LNi(Cp)X with alkylamino-substituted N-heterocyclic carbene ligands (L) and their catalytic activity in the Suzuki—Miyaura reaction
-
New nickel(ii) complexes of the general formula LNi(Cp)X (L is an N-heterocyclic carbene (NHC) ligand of the 1,2,4-triazole or imidazole series; Cp is the cyclopentadienyl anion; X = Cl, I) are reported. In these complexes, the NHC ligands (L) contain an alkylamino group at the 3 or 4 position of the heterocycle. The synthesized complexes and structurally similar complexes without an alkylamino group were tested for catalytic activity in the Suzuki—Miyaura reaction. The introduction of an alkylamino group into the NHC ligand leads to the enhancement of the catalytic activity of complexes with N,N′-diaryl-substituted NHC ligands of the imidazole series and a decrease in the activity of the complexes with N,N′-dialkyl-substituted NHC ligands of the 1,2,4-triazole series.
- Chernyshev, V. M.,Chesnokov, V. V.,Shevchenko, M. A.,Soliev, S. B.,Tafeenko, V. A.
-
p. 1281 - 1289
(2021/08/10)
-
- Integrated Suzuki Cross-Coupling/Reduction Cascade Reaction of meta-/para-Chloroacetophenones and Arylboronic Acids under Batch and Continuous Flow Conditions
-
Overcoming the incompatibility of a pair of conflicting catalysts via a flow methodology has great significance in the practical applications for multistep organic transformations. In this study, a multiple continuous-flow system is developed, which can boost the reactivity and selectivity in a sequential enantioselective cascade reaction. During this process, a periodic mesoporous organosilica-supported Pd/carbene species as a Suzuki cross-coupling catalyst is packed in the first column reactor, whereas another periodic mesoporous organosilica-supported Ru/diamine species as an asymmetric transfer hydrogenation catalyst is packed in the second column reactor. As we envisioned, the initially Pd-catalyzed cross-coupling reaction of meta-/para-chloroacetophenones and aryl boronic acids followed by the subsequentially Ru-catalyzed reduction provides chiral biarylols with enhanced yields and enantioselectivities. Furthermore, the advantages of the easy handling and the simple procedure make this system an attractive application in a scale-up preparation of optically pure organic molecules under environmentally-friendly conditions.
- Li, Yilong,Wang, Chengyi,Chen, Qipeng,Li, Hongyu,Su, Yu,Cheng, Tanyu,Liu, Guohua,Tan, Chunxia
-
supporting information
p. 2338 - 2345
(2021/07/16)
-
- New biomaterials for Ni biosorption turned into catalysts for Suzuki-Miyaura cross coupling of aryl iodides in green conditions
-
In parallel with increasing Ni production and utilisation, Ni pollution in the soil-water continuum has become an alarming and global problem. Solutions for removing Ni from industrial effluents have been widely investigated and biosorption has emerged as an efficient, cost-effective, scalable and sustainable alternative for water treatment. However, the biosorption capacity is limited by the chemical composition of the biomaterial and the Ni-enriched biomaterials are rarely valorised. In this work, the biosorption capacity of three abundant biomaterials with different chemical properties - water hyacinth, coffee grounds and pinecones - was studied before and after functionalization, and reached a maximum biosorption capacity of 51 mg g?1of Ni(ii). A bioinspired functionalization approach was investigated introducing carboxylate moieties and was conducted in green conditions. The Ni-enriched biomaterials were valorised by transformation into catalysts, which were characterised by MP-AES and XRPD. Their characterisation revealed a structure similar to nickel formate, and hence the Eco-Ni(HCOO)2catalysts were tested in Suzuki-Miyaura reactions. Several aryl iodides were successfully cross-coupled to phenylboronic acids using Eco-Ni(HCOO)2without any ligand, a mild and green base in a mixture of green solvents.
- Cases, Lucie,Adler, Pauline,Pelissier, Franck,Diliberto, Sébastien,Boulanger, Clotilde,Grison, Claude
-
p. 28085 - 28091
(2021/09/15)
-
- Synthesis of water soluble Pd-Piperidoimidazolin-2-ylidene complexes and their catalytic activities in neat water
-
Through the strategy of water soluble N-heterocyclic carbene (NHC) ligand, Pd-catalyzed reactions were developed in aqueous media. Therefore, four new piperidoimidazolinium salts (1a-d) consisting of sulfonate (a), esther (b, c) and carboxylic acid (d) functionalities and their water-soluble Pd-NHC complexes (2a-d) were synthesized. The new compounds were characterized by elemental analysis, FTIR, TGA, UV–vis and NMR spectroscopy. The catalytic activities of water soluble Pd-NHC complexes (2a-d) were investigated using the Suzuki-Miyaura (S-M) reaction and the reduction of nitroarenes. We found that the water-soluble polar or ionic groups on piperidoimidazolin-2-ylidine had an effect on the catalytic activity. The water-soluble catalyst can be recycled efficiently and reused six times with only a very slight loss of catalytic activity.
- ?ak?r, Sinem,Türkmen, Hayati
-
-
- Nickel(ii) N-heterocyclic carbene complexes as efficient catalysts for the Suzuki—Miyaura reaction
-
Catalytic activity of nickel(ii) and palladium(ii) N-heterocyclic carbene (NHC) complexes derived from imidazole, benzimidazole, and 1,2,4-triazole was comparatively evaluated in the cross-coupling reactions of aryl halides with arylboronic acids. Readily available nickel bis-NHC complexes (NHC)2NiX2 (X = Cl, Br, or I) exhibited the activity comparable to that of the structurally related palladium complexes and, consequently, can be applied as efficient catalysts for the Suzuki—Miyaura reaction.
- Astakhov, A. V.,Chernyshev, V. M.,Pasyukov, D. V.,Soliev, S. B.
-
p. 683 - 690
(2020/05/04)
-
- Aqueous Suzuki-Miyaura coupling with ultralow palladium loading and simple product separation
-
The diphosphine ligand N, N -bis(diphenylphosphanylmethyl)-aniline (bdppma) and PdCl 2afforded a Suzuki-Miyaura catalyst [(bdppm-)PdCl 2] that was highly efficient at an ultralow catalyst loading (0.001 mol%) in 20:1 H 2O-EtOH. This low catalyst loading in an aqueous solvent system permitted simple product separation by direct filtration without the need for chromatography. The ligand bdppma imparted surprisingly better reactivity than that achieved with other bidentate diphosphine ligands, but the catalytic system had a slightly narrower substrate scope than some similar Pd catalysts reported previously.
- Yang, Wei,Xu, Wen-Di,Ning, Jin-Jiao,Ren, Zhi-Gang,Young, David James
-
supporting information
p. 1303 - 1307
(2020/08/21)
-
- Visible-Light-Enhanced Suzuki–Miyaura Reactions of Aryl Chlorides in Water with Pd NPs Supported on a Conjugated Nanoporous Polycarbazole
-
The visible-light-enhanced catalytic activation of aryl chlorides for Suzuki–Miyaura cross-coupling (SMC) reactions is highly challenging because of the strength of the C?Cl bond. In this work, palladium nanoparticles (Pd NPs) were grown on a conjugated nanoporous polycarbazole (CNP), named Pd/CNP. The hybrid material Pd/CNP could catalyze the SMC reactions of aryl chlorides with arylboronic acids in water under blue LED irradiation at room temperature with high efficiency. This protocol exhibited good functional group tolerance and the catalyst could be recycled without significant loss of its catalytic activity. CNP not only provided photogenerated electrons to enrich the electron density of the Pd NPs but also generated holes for the activation of the arylboronic acids.
- Guo, Bin,Li, Hong-Xi,Zha, Cheng-Hao,Young, David James,Li, Hai-Yan,Lang, Jian-Ping
-
p. 1421 - 1427
(2019/02/26)
-
- METHODS AND COMPOSITIONS FOR INHIBITION OF DIHYDROOROTATE DEHYDROGENASE
-
Disclosed herein are compounds, 3,4,6,8-substituted-2-([1,1'-biphenyl]-4-yl)quinoline analogs, that are inhibitors of dihydroorotate dehydrogenase (DHODH) with improved pharmacokinetic properties. The disclosed compounds can be used in the treatment of a variety of disorders and diseases in which inhibition of DHODH can be clinically useful, including cancer, such as a hematological cancer, including acute myeloid leukemia (AML); graft-versus-host-diseases; autoimmune disorders; and disorders associated with T-cell proliferation. The disclosed compounds can demonstrate flip-flop kinetics when administered orally, i.e., pharmacokinetics in which the rate of absorption, rather than the rate of elimination, dominates the pharmacokinetics. The disclosed compounds can demonstrate a sustained pharmacokinetic profile instead of an immediate release profile. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
- -
-
Paragraph 0276; 0306-0307
(2020/01/11)
-
- Nickel-catalyzed cross-coupling of: O, N -chelated diarylborinates with aryl chlorides and mesylates
-
A practical nickel catalyst system consisting of readily available components, trans-NiCl(Ph)(PPh3)2/[Iprmim]I/K3PO4·3H2O in toluene, has been developed for efficient cross-coupling of 3-dimethylaminopropyl diarylborinates with aryl chlorides and mesylates. A small amount of water has been found to be crucial in achieving high efficiency in the system. The nickel catalyst system displayed remarkably higher activities to aryl chlorides and mesylates than the corresponding tosylates in cross-coupling with not only diarylborinates but also diarylborinic acids, arylboronic acids, anhydrides and trifluoroborates as indicated in control experiments. A variety of electronically various biaryls could be obtained in excellent yields by using 3-5 mol% loading of the nickel catalyst while sterically hindered biaryls were obtained in comparably lower yields.
- Ren, Chao,Zeng, Jingshu,Zou, Gang
-
supporting information
p. 1589 - 1596
(2019/01/23)
-
- Highly efficient and recyclable water-soluble fullerene-supported PdCl2 nanocatalyst in Suzuki-Miyaura cross-coupling reaction
-
A water-soluble fullerene-supported PdCl2 nanocatalyst [C60-TEGS/PdCl2] was prepared by coordination of water-soluble fullerene nanoparticles with palladium chloride. In pure water, the catalytic activity of nanocatalyst [C60-TEGS/PdCl2] for Suzuki-Miyaura cross-coupling reaction was investigated under different reaction conditions. The results showed that biphenyl compounds could be synthesized in high yields at room temperature using 0.01 mol% of [C60-TEGS/PdCl2] as the catalyst and K2CO3 as the base with the reaction time of 4 h. The catalyst was recycled five times, and the yield clearly did not decrease.
- Li, Jingbo,Huo, Ping,Zheng, Junwei,Zhou, Xiuming,Liu, Wanyun
-
p. 24231 - 24235
(2018/07/25)
-
- PRODUCTION METHOD OF COUPLING REACTION PRODUCT OF ORGANIC COMPOUND HAVING LEAVING GROUP WITH ORGANOBORON COMPOUND
-
PROBLEM TO BE SOLVED: To provide a production method with which a coupling product of the Suzuki-Miyaura cross-coupling reaction can be obtained without using any special ligand, with a practically available yield, and with an amount of catalyst of order of mol ppm. SOLUTION: In a production method, a coupling product is produced by making an organic compound having a leaving group selected from bromine atom, iodine atom, methanesulfonyloxy group, and trifluoromethanesulfonyloxy group react with an organoboron compound in the presence of a catalyst, a base and a solvent, in which the catalyst is a palladium salt with an amount of 10 mol ppm or less, the base is a carbonate, and the solvent is a mixed solvent including ethanol or isopropanol and water, and the reaction is carried out in an oxygen-containing gaseous atmosphere. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
- -
-
Paragraph 0025-0027
(2018/05/24)
-
- Acyl and Decarbonylative Suzuki Coupling of N-Acetyl Amides: Electronic Tuning of Twisted, Acyclic Amides in Catalytic Carbon-Nitrogen Bond Cleavage
-
We report the Pd-catalyzed acyl and the Ni-catalyzed biaryl Suzuki-Miyaura cross-coupling of N-acetyl-amides with arylboronic acids by selective N-C(O) cleavage. Activation of the amide bond by N-acylation provides electronically destabilized, acyclic, nonplanar amide, which readily undergoes cross-coupling with a wide range of boronic acids to produce biaryl ketones or biaryls in a highly efficient manner. Most crucially, the presented results introduce N-acetyl-amides as reactive acyclic amides in the emerging manifold of transition-metal-catalyzed amide cross-coupling. The scope and origin of high selectivity are discussed. Mechanistic studies point to remodeling of amidic resonance and amide bond twist as selectivity determining features in a unified strategy for cross-coupling of acyclic amides. Structural studies, mechanistic investigations as well as beneficial effects of the N-acyl substitution on cross-coupling of amides are reported.
- Liu, Chengwei,Li, Guangchen,Shi, Shicheng,Meng, Guangrong,Lalancette, Roger,Szostak, Roman,Szostak, Michal
-
p. 9131 - 9139
(2018/09/21)
-
- Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions
-
Bench-stable solid triorganoindium compounds have been prepared by coordination with 4-(dimethylamino)pyridine (DMAP). The solid R3In(DMAP) complexes are obtained from the corresponding solution of R3In in quantitative yield and can
- Gil-Negrete, José M.,Pérez Sestelo, José,Sarandeses, Luis A.
-
supporting information
p. 1453 - 1456
(2018/02/19)
-
- Developing potential agents against atherosclerosis: Design, synthesis and pharmacological evaluation of novel dual inhibitors of oxidative stress and Squalene Synthase activity
-
For the treatment of multifactorial and complex diseases, it has become increasingly apparent that compounds acting at multiple targets often deliver superior efficacy compared to compounds with high specificity for only a single target. Based on previous studies demonstrating the important antioxidant and anti-hyperlipidemic effect of morpholine and 1,4-benzo(x/thi)azine derivatives (A-E), we hereby present the design, synthesis and pharmacological evaluation of novel dual-acting molecules as a therapeutic approach for atherosclerosis. Analogues 1–10 were rationally designed through structural modifications of their parent compounds (A-E) in order for structure-activity relationship studies to be carried out. Most compounds showed a significant inhibition against Squalene Synthase activity exhibiting at the same time a very potent multimodal antioxidant (against lipid peroxidation and as free-radical scavengers) effect, thus bringing to light the 2-aryl-1,4-benzo(x/thia)zin-2-ol scaffold as an outstanding pharmacophore for the design of potent antioxidants. Finally, the replacement of the octahydro-1,4-benzoxazine moiety of lead compound D with its respective 1,4-benzothiazine (compound 4), although conserved (anti-hypercholesterolemic) or even improved (anti-hyperlipidemic) activity, did not preserve the anti-diabetic effect of D.
- Katselou, Maria G.,Matralis, Alexios N.,Kourounakis, Angeliki P.
-
p. 748 - 760
(2017/07/22)
-
- Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides
-
A series of bulky geometry-constrained iminopyridylpalladium chlorides were developed. The steric environment adjacent to the nitrogen atom in the pyridine rings and diimine parts enhanced the thermal stability of the palladium species. Bulkier groups at the imino group stabilized the palladium species and the corresponding palladium chlorides showed high activities in the coupling reaction of aryl chlorides.
- Lai, Yi,Zong, Zhijian,Tang, Yujie,Mo, Weimin,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Jin, Liqun,Sun, Wen-Hua,Hu, Xinquan
-
p. 213 - 221
(2017/02/15)
-
- Suzuki-Miyaura cross-coupling reaction of aryl chlorides with aryl boronic acids catalyzed by a palladium dichloride adduct of N-diphenylphosphanyl-2-aminopyridine
-
One palladium dichloride adduct of a phosphine-pyridine ligand N-diphenylphosphanyl-2-aminopyridine (L1) [(L1)PdCl2] (1) has been prepared and structurally characterized. Compound 1 can be used as an effective catalyst for the Suzuki-Miyaura cross-coupling reactions of unreactive aryl chlorides with aryl boronic acids, and worked much better than its mono- or bidentate phosphine ligands. The reactions with a wide scope of substrates proceeded to give desired products in good to excellent yields.
- Xu, Lin-Yan,Liu, Chun-Yu,Liu, Shi-Yuan,Ren, Zhi-Gang,Young, David James,Lang, Jian-Ping
-
p. 3125 - 3132
(2017/05/08)
-
- Palladium(II) Chloride Complexes of N,N′-Disubstituted Imidazole-2-thiones: Syntheses, Structures, and Catalytic Performances in Suzuki-Miyaura and Sonogashira Coupling Reactions
-
Reactions of PdCl2 with 2 equiv of N,N′-disubstituted-imidazole-2-thiones R1R2C3N2S (R1 = R2 = Me (1a), iPr (1b), Cy (1c), C6Me3H2 (1d); R1 = Me, R2 = Ph (1e)) under the different conditions afford five mononuclear complexes trans-[(R1R2C3N2S)2PdCl2] (R1 = R2 = Me (2a), iPr (2b), Cy (2c), C6Me3H2 (2d); R1 = Me, R2 = Ph (2e)) and five binuclear Pd(II) complexes [(PdCl2){μ-(R1R2C3N2S)}]2 (R1 = R2 = Me (3a), iPr (3b), Cy (3c), C6Me3H2 (3d); R1 = Me, R2 = Ph (3e)), respectively. Complexes 2a-2e are easily converted into the corresponding 3a-3e by adding equimolar PdCl2 in refluxing MeOH, while the reverse reaction is achieved at room temperature by addition of 2 equiv of 1a-1e. In 2b, 2d, and 2e, each Pd(II) holds a distorted square planar geometry completed by two trans Cl atoms and two trans S atoms. Complexes 3a-3e have a dimeric [Pd2S2] structure in which two {PdCl2} units are interlinked by two N,N′-disubstituted-imidazole-2-thiones. Each Pd(II) adopts a distorted square planar geometry accomplished by two cis Cl atoms and two cis bridging S atoms. Among them, complex 3d has the two largest C6Me3H2 groups on the 2 and 5 positions of imidazole-2-thione, the longest Pd-μ-S bond, the largest S-Pd-S angle, and displays the highest catalytic activity toward Suzuki-Miyaura and copper-free Sonogashira cross-coupling reactions, which are confirmed by density functional theory calculations. The results provide an interesting insight into the introduction of various substituent groups into the periphery ligands of coordination complex-based catalysts, which could tune their geometric structures to acquire the best catalytic activity toward organic reactions.
- Zhang, Li-Ming,Li, Hai-Yan,Li, Hong-Xi,Young, David James,Wang, Yong,Lang, Jian-Ping
-
p. 11230 - 11243
(2017/09/25)
-
- Highly Efficient Bulky α-Diimine Palladium Complexes for Suzuki-Miyaura Cross-Coupling Reaction
-
A series of bulky 9,10-dihydro-9,10-ethanoanthracene-11,12-diimine methyl palladium chloride complexes (C1—C6) with different steric and electronic substituent have been applied in Suzuki-Miyaura cross-coupling reactions. The influence of these substituents was investigated by comparing the catalytic performance of the complexes in the cross-coupling reactions and it can be found that the complex with bulky and electron-donating substituent is facilitated for the cross-coupling reaction of aryl halides with arylboronic acids under ambient atmosphere. The most active complex shows a wide substrate scope in excellent yields using very low catalyst concentration of 0.01 mol%.
- Huo, Ping,Li, Jingbo,Liu, Wanyun,Mei, Guangquan
-
p. 363 - 367
(2017/03/24)
-
- Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage
-
The first Ni-catalyzed Suzuki-Miyaura coupling of amides for the synthesis of widely occurring biaryl compounds through N-C amide bond activation is reported. The reaction tolerates a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents on both coupling partners. The reaction constitutes the first example of the Ni-catalyzed generation of aryl electrophiles from bench-stable amides with potential applications for a broad range of organometallic reactions. Breaking and making: The first nickel-catalyzed Suzuki-Miyaura coupling of amides for the synthesis of biaryl compounds through N-C amide bond cleavage is reported. The reaction tolerates a wide range of sensitive and electronically diverse substituents on both coupling partners.
- Shi, Shicheng,Meng, Guangrong,Szostak, Michal
-
p. 6959 - 6963
(2016/06/13)
-
- A 4 - (1-substituted phenylvinyl) biphenyl derivative and its preparation method and application
-
The invention relates to 4-(1-substituted-phenylvinyl)biphenyl derivatives, and a preparation method and application thereof. The structural general formula of the 4-(1-substituted-phenylvinyl)biphenyl derivatives is disclosed in the specification. The 4-(1-substituted-phenylvinyl)biphenyl derivatives can be used for preparing microtubulin inhibitors, protein kinase inhibitors and medicines for treating various cancers responding against cytotoxic activity (such as mammary cancer or colon cancer) and abnormal angiogenesis related cancers, and has the characteristics of high efficiency, low toxicity and multiplex inhibitory effects.
- -
-
Paragraph 0112-0115
(2016/10/07)
-
- Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions
-
The effect of liquid-assisted grinding has been studied using mechanical Suzuki-Miyaura reaction of aryl chlorides as the model reaction. Catalytic systems of Davephos and PCy3 are tested respectively showing strong influences from different liquids. Unexpected improvement of yield over 55% is observed using alcohols as additives, which is explained by in situ formed alkoxides and their participation in oxidative addition. Further expansion of substrates using Pd(OAc)2/PCy3/MeOH system gives desired products in good to high yields.
- Jiang, Zhi-Jiang,Li, Zhen-Hua,Yu, Jing-Bo,Su, Wei-Ke
-
p. 10049 - 10055
(2016/11/02)
-
- A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki-Miyaura reaction in pure water under air
-
Herein, we report a heterogenous catalyst (Pd@FSM) by immobilization of a novel Pd2+ sensor as promoter over mesoporous silica. Pd@FSM with a high palladium loading of ca. 11 mg g-1 exhibited superior catalytic activity for Suzuki-Miyaura cross-couplings and a catalyst loading of 0.05 mol% is typically sufficient to achieve excellent reaction yields. Notably, the reaction is typically carried out in water without removing atmospheric oxygen. The catalyst is conveniently recycled and remains highly active even after being recycled 5 times. During this process, loss of palladium from the solid support of the catalyst is negligible. Furthermore, the catalyst can be stored in air for at least three months without loss of its catalytic activity. This work provides a new approach to developing heterogeneous palladium catalysts by combing materials and fluorescent sensors.
- Cai, Qi,Liang, Gaosheng,Xu, Yufang,Qian, Xuhong,Zhu, Weiping
-
p. 60996 - 61000
(2016/07/12)
-
- Palladium-phosphine compound in catalyzing the application of the Suzuki reaction
-
The invention discloses an application of a palladium-phosphine compound to catalysis of Suzuki reaction. The palladium-phosphine compound serving as a catalyst is capable of efficiently catalyzing Suzuki reaction in ethyl alcohol. By virtue of the palladium-phosphine compound, the defects of aqueous phase reaction are overcome; the aqueous phase reaction can be carried out in the presence of an extremely low quantity of catalysts; the palladium-phosphine compound is high in applicability to substrate; the Suzuki reaction can be carried out in the pollution-free environment in the presence of a relatively small quantity of catalysts.
- -
-
Paragraph 0082-0085
(2017/02/02)
-
- N -Butylpyrrolidinone as a dipolar aprotic solvent for organic synthesis
-
Dipolar aprotic solvents such as N-methylpyrrolidinone (or 1-methyl-2-pyrrolidone (NMP)) are under increasing pressure from environmental regulation. NMP is a known reproductive toxin and has been placed on the EU "Substances of Very High Concern" list. Accordingly there is an urgent need for non-toxic alternatives to the dipolar aprotic solvents. N-Butylpyrrolidinone, although structurally similar to NMP, is not mutagenic or reprotoxic, yet retains many of the characteristics of a dipolar aprotic solvent. This work introduces N-butylpyrrolidinone as a new solvent for cross-coupling reactions and other syntheses typically requiring a conventional dipolar aprotic solvent.
- Sherwood, James,Parker, Helen L.,Moonen, Kristof,Farmer, Thomas J.,Hunt, Andrew J.
-
p. 3990 - 3996
(2016/07/21)
-
- A Polymer-Bound Monodentate-P-Ligated Palladium Complex as a Recyclable Catalyst for the Suzuki-Miyaura Coupling Reaction of Aryl Chlorides
-
A three-fold cross-linked polymer-bound phosphine (POL-Ph3P) with high phosphorus content has been prepared. The phosphorus-containing polymer forms a monodentate-P-ligated palladium complex, which shows excellent activity in Suzuki-Miyaura cross-coupling reactions of aryl chlorides. Importantly, the catalyst Pd/POL-Ph3P is highly stable and can be reused for at least 10 times without losing reactivity.
- Zhou, Yun-Bing,Li, Cun-Yao,Lin, Min,Ding, Yun-Jie,Zhan, Zhuang-Ping
-
supporting information
p. 2503 - 2508
(2015/08/18)
-
- Water-soluble salen-Pd complex as an efficient catalyst for Suzuki-Miyaura reaction of sterically hindered substrates in pure water
-
Water-soluble 2N2O-salen ligands and their palladium complexes were synthesized and used as efficient catalysts for the Suzuki-Miyaura reactions in pure water. Notably, the reactions of substrates with sterically demanding ortho substituents (aryl bromides and/or arylboronic acids) proceed smoothly to generate corresponding products with moderate to high yields using 0.5 mol % (salph)Pd (salph=N,N′-bis(4-SO3Na-salicylidene)-1,2-phenylenediamine) as the catalyst. Importantly, the catalytic system has the wide substrate scope and the high tolerance to various functional groups, including cyano, amino, nitro, methoxy, and acetyl. Moreover, the biaryl compounds were also obtained on a multi-gram scale by simple recrystallization with the system in the absence of any organic solvent, surfactant, or phase transfer agent and the catalyst was reused directly for the next cycle. Particularly, this protocol can be applied to synthesize aryl-substituted carbazolyl compounds.
- Liu, Ya-Shuai,Gu, Ning-Ning,Liu, Ping,Ma, Xiao-Wei,Liu, Yan,Xie, Jian-Wei,Dai, Bin
-
supporting information
p. 7985 - 7989
(2015/12/31)
-
- Versatile palladium(II)-catalyzed Suzuki-Miyaura coupling in ethanol with a novel, stabilizing ligand
-
Suzuki-Miyaura coupling reactions of arylboronic acids with aryl bromides were mediated by PdCl2 and bdppmapy (N,N-bis-(diphenylphosphanylmethyl)-2-aminopyridine) that both stabilizes and solubilizes the catalyst in predominantly ethanol as a solvent. Excellent yields for a wide variety of substrates were obtained under relatively mild conditions in this 'green' solvent.
- Ning, Jin-Jiao,Wang, Jian-Feng,Ren, Zhi-Gang,Young, David James,Lang, Jian-Ping
-
p. 4000 - 4006
(2015/06/02)
-
- Synthesis, characterization and X-ray structures of N-heterocyclic carbene palladium complexes based on calix[4]arenes: Highly efficient catalysts towards Suzuki-Miyaura cross-coupling reactions
-
A new series of calix[4]arene supported N-heterocyclic carbene palladium complexes were developed and fully characterized. A mono-substituted calix[4]arene was prepared through conventional procedures, following with the attachment of imidazolyl derivative groups to compose the precursors of novel NHCs ligands. Undergoing the alkylation with n-butylbromide and corresponding metallation with palladium and pyridine, original complexes were obtained. After a full characterization in solution and solid state, the evaluation of catalytic activity was taken out in Suzuki-Miyaura cross-coupling reactions, which revealed good performances.
- Ren, Hui,Xu, Yong,Jeanneau, Erwann,Bonnamour, Isabelle,Tu, Tao,Darbost, Ulrich
-
p. 2829 - 2837
(2014/04/17)
-
- Melamine and melamine-formaldehyde polymers as ligands for palladium and application to Suzuki-Miyaura cross-coupling reactions in sustainable solvents
-
The Suzuki-Miyaura cross-coupling reaction is a foundation stone of modern organic synthesis, as evidenced by its widespread use in the preparation of pharmaceuticals, agrochemicals, polymers, and other functional materials. With the prevalence of this venerable reaction in industrial synthesis, it is prudent to ensure its application adheres to the tenets of green chemistry. The introduction of cross-coupling catalysts that are active in sustainable solvents is therefore an important endeavor. In this report, a melamine-palladium complex is introduced as a versatile catalyst for the Suzuki-Miyaura cross-coupling reaction. This catalyst is soluble and active in both water and the renewable organic solvent ethyl lactate. The melamine-palladium catalyst can also be cross-linked by reaction with formaldehyde to generate an insoluble polymeric catalyst that can be recovered after the cross-coupling. The melamine-palladium system is inexpensive, easy to handle, bench-stable, and effective in catalysis in the presence of a variety of impurities (high cross-coupling yields were obtained in reactions run in unfiltered river water to illustrate this final point). Additionally, investigations reported herein revealed an intriguing relationship between catalytic efficiency and the base employed in the cross-coupling reaction. Implications for the mechanism of transmetalation in aqueous Suzuki-Miyaura cross-coupling reaction are discussed.
- Edwards, Grant A.,Trafford, Mitchell A.,Hamilton, Alaina E.,Buxton, Audrey M.,Bardeaux, Matthew C.,Chalker, Justin M.
-
p. 2094 - 2104
(2014/04/03)
-
- Efficient PdCl2-catalyzed Suzuki reactions using simple dicationic imidazolium salts as ligands in aqueous DMF
-
Three new palladium catalysts, prepared via reactions of PdCl2 with readily obtained and inexpensive dicationic imidazolium salts, have been developed for the Suzuki reaction. The pre-catalyst was formed in situ using the imidazolium ligand, ba
- Huang, Qing,Qiu, Jiabin,Li, Limei,Xu, Guohai,Zhou, Zhonggao
-
p. 661 - 665
(2014/08/18)
-
- Suzuki-Miyaura reactions promoted by a PdCl2/sulfonate-tagged phenanthroline precatalyst in water
-
This work reports Suzuki-Miyaura cross-coupling reactions of arylboronic acid with aryl halide or aryl dibromide mediated by PdCl2 (0.05mol%) and sodium 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-1-yl)butane-1-sulfonate (0.05mol%) at 100°C in water. The corresponding cross-coupling products were obtained in good to excellent yields. The catalytic system was recovered from the organic products by extraction with ether and the residual aqueous catalyst phase showed high activity after reuse of at least four cycles.
- Li, Qi,Zhang, Li-Ming,Bao, Jia-Jing,Li, Hong-Xi,Xie, Jing-Bo,Lang, Jian-Ping
-
p. 861 - 867
(2015/02/05)
-
- Organogold(I) phosphanes in palladium-catalyzed cross-coupling reactions in aqueous media
-
Cross-coupling reaction of organogold(I) phosphanes with organic electrophiles in aqueous media has been investigated. Reactions between isolated aryl-, alkenyl-, or alkynylgold(I) phosphanes and aryl halides or triflates, alkenyl halides, and allyl acetates proceed under palladium catalysis conditions at room temperature or 80 °C in water with THF as a co-solvent. The coupling reactions give good yields and are highly versatile and chemoselective, allowing the presence of free amino or hydroxy groups in the electrophile. This methodology was applied to the preparation of substituted phenylalanine esters in a demonstration that gold(I) organometallics are suitable reagents for metal-catalyzed cross-coupling reactions under protic conditions. Organogold(I) phosphanes react with organic electrophiles in aqueous media under palladium catalysis conditions. The reactions take place at room temperature or 80 °C in water with THF as co-solvent. The coupling is versatile and chemoselective and allows the presence of free amino and hydroxy groups in the electrophile. Copyright
- Pena-Lopez, Miguel,Sarandeses, Luis A.,Perez Sestelo, Jose
-
p. 2545 - 2554
(2013/06/05)
-
- Suzuki-Miyaura cross-coupling of arenediazonium salts catalyzed by alginate/gellan-stabilized palladium nanoparticles under aerobic conditions in water
-
The use of palladium nanoparticles stabilized by natural beads made of an alginate/gellan mixture in the Suzuki-Miyaura cross-coupling reaction of arenediazonium tetrafluoroborates with potassium aryltrifluoroborates (1:1 molar ratio) with loading as low as 0.01-0.002 mol% under aerobic, phosphine-, and base-free conditions in water is described. The catalyst system can be reused several times without significant loss of activity.
- Cacchi, Sandro,Caponetti, Eugenio,Casadei, Maria Antonietta,Di Giulio, Andrea,Fabrizi, Giancarlo,Forte, Giovanni,Goggiamani, Antonella,Moreno, Sandra,Paolicelli, Patrizia,Petrucci, Francesco,Prastaro, Alessandro,Saladino, Maria Luisa
-
supporting information; experimental part
p. 317 - 320
(2012/03/26)
-
- Palladium, iridium and ruthenium complexes with acyclic imino-N-heterocyclic carbenes and their application in aqua-phase Suzuki-Miyaura cross-coupling reaction and transfer hydrogenation
-
Palladium (4a-4c), iridium (5a-5c) and ruthenium (6a-6c) complexes have been prepared by in situ transmetalation from the corresponding silver complexes of acyclic imino-functionalized imidazolium chlorides [1-(Me)-imidazolium-3- {C(p-CH3-Ph)N(Ar)}]Cl (3) (Ar = 2,4,6-trimethylphenyl (3a), 2,6-diisopropylphenyl (3b) and phenyl (3c)) with [Pd(COD)Cl2], [Cp*IrCl2]2 or [Ru(p-cymene)Cl2] 2, respectively. Iridium and ruthenium complexes, 5a[PF 6]-5c[PF6], 6a[PF6]-6c[PF6], 6c[BF4], 6c[BPh4] and 6c[NTf2], were obtained directly from 5a-5c and 6a-6c through an anion-exchange process with KPF 6, NaBF4, NaBPh4 and LiNTf2 (bis(trifluoromethylsulfonyl)imide lithium), respectively. All complexes were characterized by FT-IR, 1H and 13C NMR spectroscopy and elemental analysis. Crystal structures of 4a, 5a and 6c[NTf2] show that five-membered chelate ring is formed in these complexes by the coordination of the carbene carbon and the imino nitrogen atom, and the latter two are cationic compounds with Cl- and NTf2- as counteranion respectively. The catalytic performance of Pd complexes for Suzuki-Miyaura cross-coupling reactions in pure water and Ir and Ru complexes for transfer hydrogenation of ketones and imines was tested in a wide scope of substrates. Pd complex 4b with the largest steric hinder exhibited the best performance to gain moderate to excellent yields on catalyzing Suzuki-Miyaura cross-coupling of aryl chlorides and arylboronic acids in water. While in transfer hydrogenation of various ketones, all the Ir and Ru complexes were effective with good to excellent yields. Among all these complexes, 6c[PF 6] was found most effective, and moderate yields could be obtained even in the transfer hydrogenation of imines. Moreover, different counteranions of Ru complexes are influential on catalyzing the transfer hydrogenation, with the sequence of PF6- ≈ BF4- > BPh4- > Cl- > NTf2 -.
- Guo, Xu-Qing,Wang, Ya-Nong,Wang, Dong,Cai, Li-Hua,Chen, Zhen-Xia,Hou, Xiu-Feng
-
p. 14557 - 14567
(2013/01/16)
-
- INTEGRIN-LINKED KINASE INHIBITORS
-
A number of compounds and use of the compounds in a method for treating or preventing cancer in a subject by administering to the subject a pharmaceutical composition including a compound of formula (I) or a pharmaceutically acceptable salt thereof are de
- -
-
Page/Page column 18
(2012/06/15)
-
- C,N-palladacycles containing N-heterocyclic carbene and azido ligands - Effective catalysts for Suzuki-Miyaura cross-coupling reactions
-
Azido-palladacycles containing C,N-donor and N-heterocyclic carbene ligands, [(C,N-L)Pd(N3)(NHC)] [NHC = IPr; 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene], were prepared from (i) IPr and dinuclear PdII azides, [Pd(μ-N3)(C,N-Ln)]2 [C,N-L1H = N,N′-dimethylbenzylamine; C,N-L2H = 2-(2′-thienyl)pyridine; C,N-L3H = azobenzene; C,N-L 4H = 2-(p-tolyl)pyridine], or from (ii) NaN3 and mononuclear PdII chloride, [Pd(Cl)(IPr)(C,N-Ln)], in aqueous solution. The structures of two of these products were determined by X-ray crystallography. The palladacycles showed high catalytic efficiency toward activated and nonactivated aryl bromides (at room temperature) as well as aryl chlorides (at 80 C) in Suzuki-Miyaura cross-coupling reactions. In addition, coupling reactions of aryl chlorides using potassium aryl trifluoroborates instead of phenyl boronic acid gave good-to-excellent product yields. Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides with organoboronic acid as well as potassium aryl trifluoroborates catalyzed by C,N-donor palladacycles containing N-heterocyclic carbene (NHC) and azido ligands under various conditions have been performed. Copyright
- Kim, Yong-Joo,Lee, Jung-Hyun,Kim, Taejung,Ham, Jungyeob,Zheng, Zhen Nu,Lee, Soon W.
-
p. 6011 - 6017
(2013/03/14)
-
- Cobalt-catalyzed preparation of arylindium reagents from aryl and heteroaryl bromides
-
A cobalt-bathophenanthroline catalyst has been developed for the direct preparation of a variety of arylindium reagents from the corresponding aryl and heteroaryl bromides in the presence of indium metal and lithium chloride. The thus-formed arylindium reagents undergo efficient palladium-catalyzed cross-coupling reactions with aryl iodides, tolerating various functional groups including hydroxy and free amino groups.
- Adak, Laksmikanta,Yoshikai, Naohiko
-
experimental part
p. 7563 - 7568
(2011/11/12)
-
- Identification and characterization of a novel integrin-linked kinase inhibitor
-
Integrin-linked kinase (ILK) represents a relevant target for cancer therapy in light of its role in promoting oncogenesis and tumor progression. Through the screening of an in-house focused compound library, we identified N-methyl-3-(1-(4-(piperazin-1-yl)phenyl)-5-(4′-(trifluoromethyl)-[1, 1′-biphenyl]-4-yl)-1H-pyrazol-3-yl)propanamide (22) as a novel ILK inhibitor (IC50, 0.6 μM), which exhibited high in vitro potency against a panel of prostate and breast cancer cell lines (IC50, 1-2.5 μM), while normal epithelial cells were unaffected. Compound 22 facilitated the dephosphorylation of Akt at Ser-473 and other ILK targets, including glycogen synthase kinase-3β and myosin light chain. Moreover, 22 suppressed the expression of the transcription/translation factor YB-1 and its targets HER2 and EGFR in PC-3 cells, which could be rescued by the stable expression of constitutively active ILK. Evidence indicates that 22 induced autophagy and apoptosis, both of which were integral to its antiproliferative activity. Together, this broad spectrum of mechanisms underlies the therapeutic potential of 22 in cancer treatment, which is manifested by its in vivo efficacy as a single oral agent in suppressing PC-3 xenograft tumor growth.
- Lee, Su-Lin,Hsu, En-Chi,Chou, Chih-Chien,Chuang, Hsiao-Ching,Bai, Li-Yuan,Kulp, Samuel K.,Chen, Ching-Shih
-
experimental part
p. 6364 - 6374
(2011/11/06)
-
- A robust hydrophilic pyridine-bridged bis-benzimidazolylidene palladium pincer complex: Synthesis and its catalytic application towards Suzuki-Miyaura couplings in aqueous solvents
-
A novel hydrophilic pyridine-bridged bis-benzimidazolylidene palladium pincer complex (3) acted as a highly efficient robust recyclable molecular catalyst towards Suzuki-Miyaura coupling reactions in aqueous media and tolerated various functional groups (even heterocycles) with extremely low catalyst loading. The Royal Society of Chemistry 2010.
- Tu, Tao,Feng, Xike,Wang, Zhixun,Liu, Xiyu
-
supporting information; experimental part
p. 10598 - 10600
(2011/01/10)
-
- Perfluoro-tagged, phosphine-free palladium nanoparticles supported on silica gel: Application to alkynylation of aryl halides, Suzuki-Miyaura cross-coupling, and Heck reactions under aerobic conditions
-
The utilization of perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel through fluorous-fluorous interactions (Pd np-A/FSG) or through covalent bonding to silica gel (Pd np-B) in the alkynylation of aryl halides, in the Suzuki-Miyaura cross-coupling, as well as in the Heck reaction between methyl acrylate and aryl iodides is described. The reactions are carried out under aerobic and phosphine-free conditions with excellent to quantitative product yields in each case. The catalysts are easily recovered and reused several times without significant loss of activity. The alkynylation of aryl halides (under copper-free conditions) and the Suzuki-Miyaura cross-coupling are carried out in water. The Heck reaction of methyl acrylate with aryl iodides is best performed in MeCN. The utilization of Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported.
- Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Forte, Giovanni,Petrucci, Francesco,Prastaro, Alessandro,Niembro, Sandra,Shafir, Alexandr,Vallribera, Adelina
-
supporting information; experimental part
p. 150 - 158
(2010/05/18)
-
- Palladium-indolylphosphine-catalyzed hiyama cross-coupling of aryl mesylates
-
(Chemical Equation Presented) Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)2 and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.
- So, Chau Ming,Lee, Hang Wai,Lau, Chak Po,Kwong, Fuk Yee
-
supporting information; experimental part
p. 317 - 320
(2009/07/04)
-
- Efficient palladium-catalysed carbonylative and Suzuki-Miyaura cross-coupling reactions with bis(di-tert-butylphosphino)-o-xylene
-
The use of the ligand bis(di-tert-butylphosphino)-o-xylene (dtbpx) in palladium-catalysed carbonylative and Suzuki-Miyaura cross-coupling reactions is described. Aryl and vinyl halides readily entered into the carbonylative catalytic cycle affording carboxylic acids, amides as well as primary, secondary and tertiary esters, respectively, in good yields. Aryl iodides, bromides and chlorides gave high yields of biphenyl products upon reaction with both activated and unactivated boronic acids.
- McNulty, James,Nair, Jerald J.,Sliwinski, Marcin,Robertson, Al J.
-
experimental part
p. 2342 - 2346
(2009/08/17)
-
- PdEDTA held in an ionic liquid brush as a highly efficient and reusable catalyst for Suzuki reactions in water
-
(Chemical Equation Presented) An efficient and reusable catalyst with PdEDTA immobilized in an ionic liquid brush and a green procedure have been developed for coupling aryl iodides and bromides with phenylboronic acid. These reactions were conducted in water under aerobic conditions with water-insoluble or even solid aryl halides. The protocol has the advantages of excellent yields, environmental friendliness, and catalyst recyclability. There was no apparent loss of catalyst efficiency until the 10th cycle.
- Wei, Jun-Fa,Jiao, Jiao,Feng, Jin-Juan,Lv, Jing,Zhang, Xi-Ru,Shi, Xian-Ying,Chen, Zhan-Guo
-
supporting information; experimental part
p. 6283 - 6286
(2009/12/24)
-