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Synthesis 2019; 51(13): 2667-2677
DOI: 10.1055/s-0037-1611788
DOI: 10.1055/s-0037-1611788
special topic
Hitchhiker’s Guide to Reductive Amination
This work was supported by the RFBR (grant numbers 18-33-20065, 18-03-00839) and the Council of the President of the Russian Federation (Grant for Young Scientists No. MK- 1736.2019.3). D.C. is grateful to the generous support of RUDN "5-100" program.Further Information
Publication History
Received: 14 February 2019
Accepted after revision: 12 March 2019
Publication Date:
17 April 2019 (online)
Published as part of the Special Topic Amination Reactions in Organic Synthesis
Abstract
A comparative study of various widely used methods of reductive amination is reported. Specifically, such reducing agents as H2, Pd/C, hydride reagents [NaBH4, NaBH3CN, NaBH(OAc)3], and CO/Rh2(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.
Key words
reductive amination - selectivity - atom efficiency - borohydride - hydrogen - palladium - carbon monoxideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611788.
- Supporting Information
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