Pd-NHC catalyzed Suzuki cross-coupling of benzyl ammonium salts

A palladium-catalyzed Suzuki cross-coupling of benzyl ammonium triflates via activation of a Csp(3)-N bond to construct a Csp(3)-Csp(2) bond is described. Various boronic acids can be coupled with a range of benzylamine-derived quaternary ammonium salts in 1:1 molar ratio by the bench-stable N-heterocyclic carbene palladium complex, SIPr-PdCl2-Py to afford diarylmethane derivatives. This reaction exhibits a wide substrate scope and functional group tolerance. Direct arylation of benzylamine in a one-pot process and the gram-scale reaction can be performed successfully.

Automated summary

This article describes a palladium-catalyzed Suzuki cross-coupling reaction of benzyl ammonium triflates via activation of a Csp(3)-N bond to construct a Csp(3)-Csp(2) bond. The reaction exhibits a wide substrate scope and functional group tolerance, and can be successfully performed in a one-pot process.