1839-72-1Relevant articles and documents
Insight into the palladium-catalyzed oxidative arylation of benzofuran: Heteropoly acid oxidants evoke a Pd(II)/Pd(IV) mechanism
Pereira, Kyle C.,Porter, Ashley L.,Potavathri, Shathaverdhan,Lebris, Alexis P.,Deboef, Brenton
, p. 4429 - 4435 (2013)
The effects of oxidant and organic acid additives on the oxidative cross-coupling reactions of electron rich heterocycles, such as benzofuran with benzene were studied. Both regioselectivity and reaction rate could be controlled by varying the condition p
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Hercouet,Le Corre
, p. 2145 (1979)
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Photolabile benzoin and furoin esters of a biologically active peptide
Peach, Josephine M.,Pratt, Andrew J.,Snaith, John S.
, p. 10013 - 10024 (1995)
Benzoin and furoin esters of N-carbobenzyloxyglycylphenylalanine were prepared and photolyzed under a variety of conditions. The photochemistry of peptide-derived benzoin esters is more efficient than that of furoin esters and is appropriate for the photo
A stereoselective synthesis of 1,2-diarylethenyl ethyl ethers via the carbocupration-cross coupling sequence
Kato, Noriyasu,Miyaura, Norio
, p. 13347 - 13354 (1996)
The synthesis of vinyl ethers [Ph(EtO)C= CHAr] was carried out by a sequence of carbocupration of ethoxyethyne with phenylcopper(I) followed by the palladium-catalyzed crosscoupling reaction of the resulting 2-ethoxyvinylcopper(I) complex with iodoarenes. The 2-ethoxyvinylcopper(I) species thus obtained were sufficiently stable to undergo the cross-coupling reaction at 0-20°C in the presence of a catalytic amount of PdCl2(dppf) or Pd(PPh3)4 and 1 equivalent of ZnBr2. The syntheses of 2-phenylbenzo[b]furan and 2-phenylindole demonstrated the utility of the present one-pot, two-step procedure for the synthesis of vinyl ethers.
Mild and efficient cyclization reaction of 2-ethynylaniline derivatives to indoles in aqueous medium
Hiroya, Kou,Itoh, Shin,Sakamoto, Takao
, p. 10958 - 10964 (2005)
Results of the optimized cyclization reaction of 2-ethynylaniline derivatives to indoles catalyzed by copper(II) salts are described. The reactions can be carried out in a mixture of H2O and MeOH in the presence of 1-ethylpiperidine at room tem
Novel cyclization to benzofurans in the reaction of alkynyl(p-phenylene) bisiodonium ditriflates with phenoxide anion
Kitamura, Tsugio,Zheng, Lei,Taniguchi, Hiroshi,Sakurai, Makoto,Tanaka, Ryuichi
, p. 4055 - 4058 (1993)
Reaction of alkynyl(p-phenylene)bisiodonium ditriflates (2) with sodium phenoxide in methanol provides 2-substituted benzofurans (3). This result indicates that β-phenoxyalkylidenecarbenes generated by the reaction with phenoxide anion undergo novel intramolecular aromatic C-H insertion to afford benzofurans.
Palladium-Catalyzed Aryl-Furanylation of Alkenes: Synthesis of Benzofuran-Containing 3,3-Disubstituted Oxindoles
Chen, Shufeng,Han, Kaiming,Qi, Hongbo
, p. 9384 - 9395 (2021)
A novel palladium-catalyzed aryl-furanylation of alkenes is described. This protocol provided a straightforward route to the synthesis of various benzofuran-containing 3,3-disubstitutedoxindole derivatives bearing a quarternary carbon center. In the cascade process, one C(sp2)-O bond, two C(sp2)-C(sp3) bonds, an oxindole, and a furan ring are formed in a single chemical operation.
A new hybrid nanocatalyst based on Cu-doped Pd-Fe3O4 for tandem synthesis of 2-phenylbenzofurans
Woo, Hyunje,Kim, Daeho,Park, Ji Chan,Kim, Ji Woong,Park, Sungkyun,Lee, Jae Myung,Park, Kang Hyun
, p. 20992 - 20998 (2015)
We report a one-pot synthesis of hybrid nanocomposites of Cu-doped Pd-Fe3O4via controlled thermal decomposition of Fe(CO)5 and reduction of Pd(OAc)2 and Cu(acac)2. Sodium oleate, used as a capping age
Reinvestigation of the noncatalyzed coupling of aryllithium with haloarene: A novel aromatic nucleophilic substitution pathway
Becht, Jean-Michel,Gissot, Arnaud,Wagner, Alain,Mioskowski, Charles
, p. 3209 - 3215 (2003)
Noncatalyzed coupling reactions of aryllithiums and haloarenes proceed not only through the well-known aryne route but also, in some cases, through a novel addition-elimination pathway. Indeed, ortho-chloro- and ortho-bromomethoxyarenes lead selectively to the corresponding ortho-biaryls through a chelation-driven aromatic nucleophilic substitution pathway. Contrary to common belief, such noncatalyzed coupling reactions often proceed with high regioselectivity and high yield. These results underline the potency of such simple reactions and open up a straightforward access to a wide range of biaryl structures; this also appears particularly useful for large-scale and biaryl building-block syntheses, as only cheap and readily available substrates are involved.
Highly active heterogeneous palladium nanoparticle catalysts for homogeneous electrophilic reactions in solution and the utilization of a continuous flow reactor
Huang, Wenyu,Liu, Jack Hung-Chang,Alayoglu, Pinar,Li, Yimin,Witham, Cole A.,Tsung, Chia-Kuang,Toste, F. Dean,Somorjai, Gabor A.
, p. 16771 - 16773 (2010)
A highly active heterogeneous Pd-nanoparticle catalyst for the intramolecular addition of phenols to alkynes was developed and employed in a continuous flow reaction system. Running the reaction in flow mode revealed reaction kinetics, such as the activat
A Pt-cluster-based heterogeneous catalyst for homogeneous catalytic reactions: X-ray absorption spectroscopy and reaction kinetic studies of their activity and stability against leaching
Li, Yimin,Liu, Jack Hung-Chang,Witham, Cole A.,Huang, Wenyu,Marcus, Matthew A.,Fakra, Sirine C.,Alayoglu, Pinar,Zhu, Zhongwei,Thompson, Christopher M.,Arjun, Arpana,Lee, Kihong,Gross, Elad,Toste, F. Dean,Somorjai, Gabor A.
, p. 13527 - 13533 (2011)
The design and development of metal-cluster-based heterogeneous catalysts with high activity, selectivity, and stability under solution-phase reaction conditions will enable their applications as recyclable catalysts in large-scale fine chemicals producti
New Palladium – ZrO2 Nano-Architectures from Thermal Transformation of UiO-66-NH2 for Carbonylative Suzuki and Hydrogenation Reactions
Alsalahi, Waleed,Augustyniak, Adam W.,Tylus, W?odzimierz,Trzeciak, Anna M.
supporting information, (2021/12/22)
The new nanocomposites, Pd/C/ZrO2, PdO/ZrO2, and Pd/PdO/ZrO2, were prepared by thermal conversion of Pd@UiO-66-Zr?NH2 (MOF) in nitrogen or air atmosphere. The presence of Pd nanoparticles, uniformly distributed on the ZrO2 or C/ZrO2 matrix, was evidenced by transmission electron microscopy, scanning electron microscopy (SEM), Raman and X-ray Photoelectron Spectroscopy (XPS) methods. All pyrolysed composites retained the shape of the MOF template. They catalyze carbonylative Suzuki coupling under 1 atm CO with an efficiency significantly higher than the original Pd@UiO-66-Zr?NH2. The most active PdO/ZrO2 composite, formed benzophenone with TOF up to 1600 h?1, while by using Pd@UiO-66-Zr?NH2, much lower TOF values, 51–95 h?1, were achieved. After the reaction, PdO/ZrO2 was recovered with the same composition and catalytic activity. Very good results were also obtained in the transfer hydrogenation of benzophenones to alcohols with Pd/C/ZrO2 and PdO/ZrO2 catalysts under microwave irradiation.
Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate
Liu, Juyan,Tian, Miaomiao,Li, Ankun,Ji, Liangshuo,Qiu, Di,Zhao, Xia
supporting information, (2021/02/01)
A Br?nsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst.
Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents
Wen, Chang,Wu, Chuan,Luo, Ruiqiang,Li, Qinghan,Chen, Feng
, p. 3847 - 3861 (2021/07/02)
A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.
