Coupling of thiols and aromatic halides promoted by diboron derived super electron donors

Abstract

We have proven that pyridine–boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a S_RN1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.