DIC-borane-catalyzed selective methylation of primary amines with CO2 using boranes as reducing agents

被引：6

作者：

Zhang, He ^{[1
]}

Zhang, Yanmeng ^{[1
]}

Gao, Ke ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticides & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan, Hubei, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 10期

关键词：

CARBON-DIOXIDE; N-FORMYLATION; REDUCTIVE FUNCTIONALIZATION; MOLECULAR-HYDROGEN; MILD; TRANSFORMATION; HYDROSILANES; BLOCK;

D O I：

10.1039/d3qo00058c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective reductive N-methylation and N,N-dimethylation of primary amines using CO2 are some of the most significant challenges faced by organic chemists. Herein, we report the highly selective N,N '-diisopropylcarbodiimide-catalyzed methylation of primary amines using 1 atm CO2 under metal-free conditions. Borane-piperazine and borane-trimethylamine complexes were used as reducing agents for the N-methylation and N,N-dimethylation of various aromatic primary amines, respectively, in the presence of CO2. Mechanistic studies suggest that the selectivity of methylation is controlled by the steric effects of amines and boranes.

引用

页码：2491 / 2497

页数：7

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