- Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations
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Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys
- Campbell, Joanna L. P.,Davies, Christopher D.,Ho?ek, Jan,Ko?ovsky, Pavel,Kysilka, Ond?ej,Popov, Kirill K.,Pour, Milan
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p. 920 - 943
(2022/01/27)
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- Hitchhiker's Guide to Reductive Amination
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A comparative study of various widely used methods of reductive amination is reported. Specifically, such reducing agents as H 2, Pd/C, hydride reagents [NaBH 4, NaBH 3 CN, NaBH(OAc) 3 ], and CO/Rh 2 (OAc) 4 system were considered. For understanding the selectivity and activity of the reducing agents reviewed herein, different classes of starting materials were tested, including aliphatic and aromatic amines, as well as aliphatic and aromatic aldehydes and ketones. Most important advantages and drawbacks of the methods, such as selectivity of the target amine formation and toxicity of the reducing agents were compared. Methods were also considered from the viewpoint of green chemistry.
- Afanasyev, Oleg I.,Chusov, Denis,Makarova, Maria,Podyacheva, Evgeniya,Tsygankov, Alexey A.
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supporting information
p. 2667 - 2677
(2019/06/19)
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- Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles
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N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.
- Senthamarai, Thirusangumurugan,Murugesan, Kathiravan,Natte, Kishore,Kalevaru, Narayana V.,Neumann, Helfried,Kamer, Paul C. J.,Jagadeesh, Rajenahally V.
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p. 1235 - 1240
(2018/02/09)
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- Cyclobutadiene Metal Complexes: A New Class of Highly Selective Catalysts. An Application to Direct Reductive Amination
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A catalyst of a new type, cyclobutadiene complex [(C4Et4)Rh(p-xylene)]PF6, was found to promote selective reductive amination in the presence of carbon monoxide under mild conditions (1-3 bar, 90 °C). The reaction demonstr
- Afanasyev, Oleg I.,Tsygankov, Alexey A.,Usanov, Dmitry L.,Perekalin, Dmitry S.,Shvydkiy, Nikita V.,Maleev, Victor I.,Kudinov, Alexander R.,Chusov, Denis
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p. 2043 - 2046
(2016/03/15)
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- Dual Role of Acetate in Copper(II) Acetate Catalyzed Dehydrogenation of Chelating Aromatic Secondary Amines: A Kinetic Case Study of Copper-Catalyzed Oxidation Reactions
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Copper(II) acetate is a frequent empirical choice of the copper source in copper(II)-mediated redox reactions. The effect of the acetate counterion appears crucial but has not been adequately investigated. Herein, we report that copper(II) acetate catalyz
- Sreenath, Kesavapillai,Yuan, Zhao,Macias-Contreras, Miguel,Ramachandran, Vasanth,Clark, Ronald J.,Zhu, Lei
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p. 3728 - 3743
(2016/08/19)
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- Copper-Catalyzed para-Selective C-H Amination of Electron-Rich Arenes
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A one-pot two-step method for para-selective C-H amination of carbocyclic arenes comprises the in situ formation of unsymmetrical diaryl-λ3-iodanes followed by their Cu(I)-catalyzed reaction with a range of N-unprotected amines.
- Berzina, Beatrise,Sokolovs, Igors,Suna, Edgars
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p. 7008 - 7014
(2015/11/23)
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- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Compounds of Formula I with activity against HIV, including pharmaceutical compositions and methods for using these compounds in treating human immunodeficiency virus (HIV) infection, are set forth: Formula :(I)
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Page/Page column 66
(2015/05/06)
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- Molecular iodine catalyzed transfer hydrogenation: Reduction of aldimines, ketimines, and α-imino esters
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An efficient and practical protocol for the reduction of aldimines, ketimines, and α-imino esters in the presence of catalytic amount of molecular iodine with Hantzsch ester at ambient temperature afforded the corresponding amines in excellent yields.
- Bachu, Prabhakar,Zhu, Chen,Akiyama, Takahiko
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supporting information
p. 3977 - 3981
(2013/07/25)
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- Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor
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A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline an
- Zhu, Chen,Akiyama, Takahiko
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supporting information; experimental part
p. 416 - 418
(2012/02/05)
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- Br?nsted acid catalyzed reductive amination with benzothiazoline as a highly efficient hydrogen donor
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Reductive amination of aldehyde and amine proceeded smoothly in the presence of benzothiazoline as efficient hydrogen source by means of 20 mol% trifluoroacetic acid to give the corresponding amines in excellent yields. Hydrogen-donor abilities of benzothiazoline, benzimidazoline, and benzoxazoline were compared. Georg Thieme Verlag Stuttgart - New York.
- Zhu, Chen,Akiyama, Takahiko
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supporting information; experimental part
p. 1251 - 1254
(2011/06/28)
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