10359-18-9Relevant articles and documents
Reductive amination of acetals by anilines in the presence of triethylsilane and iodine
Zhang, Xue-Lin,Yu, Pan,Wu, Yong-Wei,Wu, Qin-Pei,Zhang, Qing-Shan
, p. 261 - 264 (2014)
A mild and efficient method for N-alkylation of aromatic amines with various acetals such as aryl, alkyl, cyclic and acyclic acetals was developed. A number of aromatic amines bearing electron-donating or electron-withdrawing substituents were directly alkylated by acetals with excellent yields. The method uses a catalytic amount of I2 and triethylsilane as the hydride source without a metal present. Monoalkylation with excellent chemoselectivity was observed.
Br?nsted Acid-Catalyzed Transfer Hydrogenation of Imines and Alkenes Using Cyclohexa-1,4-dienes as Dihydrogen Surrogates
Chatterjee, Indranil,Oestreich, Martin
, p. 2463 - 2466 (2016)
Cyclohexa-1,4-dienes are introduced to Br?nsted acid-catalyzed transfer hydrogenation as an alternative to the widely used Hantzsch dihydropyridines. While these hydrocarbon-based dihydrogen surrogates do offer little advantage over established protocols in imine reduction as well as reductive amination, their use enables the previously unprecedented transfer hydrogenation of structurally and electronically unbiased 1,1-di- and trisubstituted alkenes. The mild procedure requires 5.0 mol % of Tf2NH, but the less acidic sulfonic acids TfOH and TsOH work equally well.
An efficient catalytic reductive amination: A facile one-pot access to 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones by using B(C 6 F 5 ) 3 /NaBH 4
Nagarsenkar, Atulya,Prajapti, Santosh Kumar,Babu, Bathini Nagendra
, p. 711 - 716 (2015)
An efficient combination of B(C6F5)3 and NaBH4 was developed for direct reductive amination of aldehydes. A wide range of functional groups such as ester, nitro, nitrile, halogen, alkene, heterocycles were tolerated. Also, acid sensitive protecting groups like TBDMS and TBDPS were not affected. In addition, the present methodology was extended for tandem amination-amidation of 3-formyl-indole-2-carboxylic acids with substituted anilines to afford 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones. [Figure not available: see fulltext.]
One-pot reductive amination of carbonyl compounds using sodium borohydride-amberlyst 15
Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Mahdavi, Nastaran
, p. 951 - 956 (2010)
A fast, efficient, and high-yielding method for the preparation of amines by reductive amination of aldehydes and ketones using sodium borohydride in the presence of Amberlyst 15 in tetrahydrofuran and under solvent-free conditions at room temperature is described.
A novel method for the reduction of imines using the system silane/MoO 2Cl2
Fernandes, Ana C.,Rom?o, Carlos C.
, p. 8881 - 8883 (2005)
A novel catalytic system, silane/MoO2Cl2 (10 mol %), for the reduction of imines in excellent to moderate yields and chemoselectivity was designed. These results extend the scope of the use of MoO 2Cl2 as an eff
1-Acetyl-2,3-dimethylimidazolidine: A novel organic reductant for transfer hydrogenation
Li, Donghong,Zhang, Yongbin,Zhou, Guofu,Guo, Wei
, p. 225 - 228 (2008)
1-Acetyl-2,3-dimethylimidazolidine was synthesized and was shown to be able to directly reduce a series of aromatic, aliphatic and α,β- unsaturated aldehydes as well as imines in high yields. Georg Thieme Verlag Stuttgart.
GaCl3-catalyzed [4+2] annulations of allyltrimethylsilane and trimethyl(propargyl)silane with aldimines
Hirashita, Tsunehisa,Kawai, Daisuke,Araki, Shuki
, p. 5421 - 5424 (2007)
The GaCl3-catalyzed reaction of allyltrimethylsilane and aldimines gave tetrahydroquinolines in good yields. Similarly, 4-methylquinoline was obtained by using trimethyl(propargyl)silane via a dehydrogenation process.
New heteroaromatic azo compounds based on pyridine, isoxazole, and benzothiazole for efficient and highly selective amidation and mono-N-benzylation of amines under Mitsunobu conditions
Iranpoor, Nasser,Firouzabadi, Habib,Khalili, Dariush
, p. 923 - 934 (2010)
4,4′-Azopyridine (2c) is used in conjunction with triphenylphosphine for the efficient conversion of carboxylic acids into amides via Mitsunobu reaction with primary and secondary aliphatic and aromatic amines. The highly selective amidation of only primary aromatic amines with new heterogeneous azo compounds based on benzothiazole 2d and isoxazole 2e is also described. These azo compounds 2c-2e can also be applied for selective mono-N-benzylation of primary aromatic amines. The solid side product heteroaromatic hydrazines obtained under the developed Mitsunobu conditions are easily separated by simple filtration and can be reoxidized to azo compounds for further use.
Metal-free hydrogen activation and hydrogenation of imines by 1,8-bis(dipentafluorophenylboryl)naphthalene
Jiang, Chunfang,Blacque, Olivier,Berke, Heinz
, p. 5518 - 5520 (2009)
In the presence of 2,2,6,6-tetramethylpiperidine (TMP) 1,8- bis(dipentafluorophenylboryl)naphthalene has been found to activate H 2 and to hydrogenate various imines under mild conditions.
Thiourea-catalyzed transfer hydrogenation of aldimines
Zhang, Zhiguo,Schreiner, Peter R.
, p. 1455 - 1457 (2007)
The present letter reports on the thiourea-catalyzed transfer hydrogenation of imines through hydrogen-bonding activation with Hantzsch 1,4-dihydropyridine as the hydrogen source. A variety of aromatic as well as aliphatic aldimines can be reduced to give
Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols
Beller, Matthias,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kadam, Ravishankar G.,Li, Xinmin,Ma, Zhuang,Petr, Martin,Zbo?il, Radek,Zhou, Bei
, p. 111 - 117 (2022/01/06)
A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
High-Throughput Screening of Reductive Amination Reactions Using Desorption Electrospray Ionization Mass Spectrometry
Cooks, R. Graham,Ferreira, Christina R.,Li, Yangjie,Logsdon, David L.,Paschoal Sobreira, Tiago Jose,Thompson, David H.
supporting information, p. 1647 - 1657 (2020/10/26)
This study describes the latest generation of a high-throughput screening system that is capable of screening thousands of organic reactions in a single day. This system combines a liquid handling robot with desorption electrospray ionization (DESI) mass spectrometry (MS) for a rapid reaction mixture preparation, accelerated synthesis, and automated MS analysis. A total of 3840 unique reductive amination reactions were screened to demonstrate the throughputs that are capable with the system. Products, byproducts, and intermediates were all monitored in full-scan mass spectra, generating a complete view of the reaction progress. Tandem mass spectrometry experiments were conducted to verify the identity of the products formed. The amine and electrophile reactivity trends represented in the data match what is expected from theory, indicating that the system accurately models the reaction performance. The DESI results correlated well with those generated using more traditional mass spectrometry techniques like liquid chromatography-mass spectrometry, validating the data generated by the system.
