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

A family of commercially available organolithium compounds were found to effectively catalyze the heterodehydrocoupling of silanes and amines under ambient conditions. Ubiquitous n BuLi (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.