4.7 Article

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

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 10, Pages 2491-2497

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d3qo00058c

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The selective reductive N-methylation and N,N-dimethylation of primary amines using CO2 is challenging. This study reports a highly selective N,N'-diisopropylcarbodiimide-catalyzed methylation of primary amines using 1 atm CO2 under metal-free conditions. The selectivity of methylation is controlled by the steric effects of amines and boranes.
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.

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