Nickel‐Catalyzed N‐Alkylation of Acylhydrazines and Arylamines Using Alcohols and Enantioselective Examples

A borrowing‐hydrogen reaction between amines and alcohols is an atom‐economic way to prepare alkylamines, ideally with water as the sole byproduct. Herein, nickel catalysts are used for direct N‐alkylation of hydrazides and arylamines using racemic alcohols. Moreover, a nickel catalyst of (S)‐binapi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-11, Vol.56 (46), p.14702-14706
Main Authors: Yang, Peng, Zhang, Caili, Ma, Yu, Zhang, Caiyun, Li, Aijie, Tang, Bo, Zhou, Jianrong Steve
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Alkylamines
Alkylation
amination
Amines
Atom economy
Catalysis
Catalysts
Enantiomers
Hydrazides
hydrogen transfer
Nickel
Organic compounds
P ligands
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Summary:A borrowing‐hydrogen reaction between amines and alcohols is an atom‐economic way to prepare alkylamines, ideally with water as the sole byproduct. Herein, nickel catalysts are used for direct N‐alkylation of hydrazides and arylamines using racemic alcohols. Moreover, a nickel catalyst of (S)‐binapine was used for an asymmetric N‐alkylation of benzohydrazide with racemic benzylic alcohols. Hydrogen autotransfer: Nickel catalysts are used for direct N‐alkylation of hydrazides and arylamines using racemic alcohols. The reaction proceeds by a hydrogen‐borrowing pathway. Also described is an asymmetric version of the reaction of N‐acylhydrazines.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201708949