Synthesis 2019; 51(13): 2667-2677
DOI: 10.1055/s-0037-1611788
special topic
© Georg Thieme Verlag Stuttgart · New York

Hitchhiker’s Guide to Reductive Amination

Evgeniya Podyacheva
a  Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation
,
Oleg I. Afanasyev
a  Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation
,
Alexey A. Tsygankov
a  Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation
,
Maria Makarova
a  Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation
b  Dmitry Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russian Federation
,
Denis Chusov*
a  Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation
c  Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow 117198, Russian Federation   Email: denis.chusov@gmail.com
d  Moscow Institute of Physics and Technology, 9 Institutskiy per., Dolgoprudny, Moscow Region, 141700, Russian Federation
› Author Affiliations
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 (eFirst)

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.

Supporting Information

 
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