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 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. This study demonstrates one of the most straightforward methodologies for coupling silanes and amines under mild conditions, arguing for the use of commonplace organolithium reagents as routine catalysts for Si–N bond forming reactions.