Hitchhiker’s Guide to Reductive Amination

Evgeniya Podyacheva; Oleg I. Afanasyev; Alexey A. Tsygankov; Maria Makarova; Denis Chusov

doi:10.1055/s-0037-1611788

Synthesis, Table of Contents

Synthesis 2019; 51(13): 2667-2677
DOI: 10.1055/s-0037-1611788

special topic

Hitchhiker’s Guide to Reductive Amination

Evgeniya Podyacheva

^aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation

,

Oleg I. Afanasyev

^aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation

,

Alexey A. Tsygankov

^aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation

,

Maria Makarova

^aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation

^bDmitry Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russian Federation

,

Denis Chusov*

^aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Vavilova 28, Moscow 119991, Russian Federation

^cPeoples’ Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow 117198, Russian Federation Email: denis.chusov@gmail.com

^dMoscow Institute of Physics and Technology, 9 Institutskiy per., Dolgoprudny, Moscow Region, 141700, Russian Federation

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Abstract

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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 monoxide

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References

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