Commercially available organolithium compounds as effective, simple precatalysts for silicon–nitrogen heterodehydrocoupling

Abstract

A family of commercially available organolithium compounds were found to effectively catalyze the heterodehydrocoupling of silanes and amines under ambient conditions. Ubiquitous nBuLi (1) was utilized as the benchmark catalyst, where an array of primary, secondary, and tertiary arylsilanes were coupled to electron-donating amines, affording aminosilanes in high conversions with short reaction times. Preliminary mechanistic analysis is consistent with a nucleophilic-type system that involves the formation of a hypervalent silicon intermediate. This work underscores the accessibility of Si–N heterodehydrocoupling, with organolithium reagents emerging as some of the most straightforward and cost-effective precatalysts for this transformation.