Citation: Huang Yan, Deng Wei, Lin Bo-Lin. Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis[J]. Chinese Chemical Letters, ;2020, 31(1): 111-114. doi: 10.1016/j.cclet.2019.04.064 shu

Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis

Huang Yan ^a ,
Deng Wei ^a,*, ,
Lin Bo-Lin ^b,*,

a.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China
b.
School of Technology and Physical Science, ShanghaiTech University, Shanghai 201210, China

wdeng@shu.edu.cn

linbl@shanghaitech.edu.cn

Received Date: 29 January 2019
Revised Date: 22 March 2019
Accepted Date: 28 April 2019
Available Online: 29 January 2019

Figures(3)

The construction of N-methyl amine moieties is an important reaction that has found numerous applications. Development of new methylation agents that are more environmentally benign than classical agents, such as iodomethane and methyl sulfate, is still highly desirable. Herein, we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis. The present protocol operates under transition-metal-free and air-tolerant conditions. Both the catalyst, K₂HPO₄, and the reductant, polymethylhydrosiloxane (PMHS), are cheap and easily separable from the crude reaction product mixture. Mechanistic investigations suggest that the reaction occur through the formation of an acetal intermediate followed by the C-N bond formation.
- Air-tolerant,
- N-Methylation,
- Formic acid,
- Simple inorganic bas,
- Transition-metal-free
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