SET processes in Lewis acid–base reactions: the tritylation of N-heterocyclic carbenes

Abstract

Reactions between N-heterocyclic carbenes (NHCs) and the trityl cation, [Ph₃C]⁺, give covalent adducts of type [NHC–CPh₃]⁺ and/or [NHC–C₆H₅–CPh₂]⁺. EPR spectroscopy, UV-Vis analyses, and trapping experiments imply that adduct formation involves carbene radical cations and the trityl radical. The results demonstrate that single electron transfer (SET) processes should be considered for reaction of NHCs with oxidizing Lewis acids.