Direct N‐Alkylation of Amines with Alcohols Catalyzed by N‐Heterocyclic Carbene Cobalt‐Pincer Catalyst under Mild Conditions

Alcohols are widely available and can be derived from renewable resources. Catalytic alcohol amination for N‐alky amine synthesis using the borrowing hydrogen strategy is an environmentally benign and prominent sustainable method, which produces water as the sole byproduct. However, expensive noble...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2024-03, Vol.13 (3), p.n/a
Main Authors: Liu, Xin, Ge, Yilei, Yang, Yang, Zhang, Minghe, Yang, Siqi, Lan, Xiaobing
Format: Article
Language:English
Subjects:
Alcohols
Alkylation
Amines
Aniline
Borrowing hydrogen
Carbenes
Catalysts
Cobalt
Cobalt catalysis
Functional groups
Green chemistry
Hydrogen
N-alkylation
N-heterocyclic carbene
Noble metals
Reaction mechanisms
Renewable resources
Substrates
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Summary:Alcohols are widely available and can be derived from renewable resources. Catalytic alcohol amination for N‐alky amine synthesis using the borrowing hydrogen strategy is an environmentally benign and prominent sustainable method, which produces water as the sole byproduct. However, expensive noble metals are generally employed for this transformation, while the nonprecious metal‐based catalysts were also known for this reaction and have attracted considerable attention recently. Herein, an efficient N‐alkylation of amines with alcohols using base‐metal cobalt catalysts is reported. This reaction is catalyzed by an N‐heterocyclic carbene cobalt‐pincer catalyst and the reaction operates simply and under mild conditions. Various alcohol and aniline substrates and functional groups including nitrile, ether, thioether and alkene could be well tolerated. Moreover, experimental studies and DFT calculations were also performed to illustrate the reaction mechanism. Our results suggest that the N‐alkylation reaction proceeds via a hydrogen autotransfer mechanism. Herein, we report an efficient N‐alkylation of amines with alcohols using N‐heterocyclic carbene cobalt‐pincer catalyst under mild conditions. Various alcohol and aniline substrates and functional groups including nitrile, ether, thioether and alkene could be well tolerated. Moreover, experimental studies and DFT calculations were also performed to illustrate the reaction mechanism.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300551