Manganese‐Catalyzed Mono‐N‐Methylation of Aliphatic Primary Amines without the Requirement of External High‐Hydrogen Pressure

Author:

Ji Jiale1,Huo Yinghao1,Dai Zhaowen1,Chen Zhening2,Tu Tao13ORCID

Affiliation:

1. Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Department of Chemistry Fudan University 2005 Songhu Road Shanghai 200438 China

2. State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences 155 Yangqiao West Road Fuzhou 350002 China.

3. State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 354 Fenglin Road Shanghai 200032 China

Abstract

AbstractThe synthesis of mono‐N‐methylated aliphatic primary amines has traditionally been challenging, requiring noble metal catalysts and high‐pressure H2 for achieving satisfactory yields and selectivity. Herein, we developed an approach for the selective coupling of methanol and aliphatic primary amines, without high‐pressure hydrogen, using a manganese‐based catalyst. Remarkably, up to 98 % yields with broad substrate scope were achieved at low catalyst loadings. Notably, due to the weak base‐catalyzed alcoholysis of formamide intermediates, our novel protocol not only obviates the addition of high‐pressure H2 but also prevents side secondary N‐methylation, supported by control experiments and density functional theory calculations.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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