Catalytic C–H Functionalization of Trimethylamine

Abstract

Carbon–carbon bond-forming hydroaminoalkylation reactions between trimethylamine and alkynes, alkenes, allenes, or a methylenecyclopropane (MCP) are achieved in the presence of titanium catalysts. The reactions take place by C–H bond activation at the methyl group of trimethylamine and therefore offer flexible and direct methods for the C–H functionalization of trimethylamine. The importance of the developed procedures for the synthesis of pharmaceutically relevant dimethylaminomethyl-substituted products is underlined by a straightforward synthesis of the antidepressant butriptyline.

Key words

amines - C–H activation - hydroaminoalkylation - titanium - trimethylamine

Publication History

Received: 07 July 2023

Accepted after revision: 21 September 2023

Accepted Manuscript online:
21 September 2023

Article published online:
30 October 2023

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