An Unexpected Synthesis of 2-Sulfonylquinolines via Deoxygenative C2-Sulfonylation of Quinoline N-Oxides with Sulfonyl Chlorides

A mild, efficient and practical protocol for the preparation of 2-sulfonylquinolines through CS₂/Et₂NH-induced deoxygenative C2-H sulfonylation of quinoline N-oxides with readily available RSO₂Cl was developed. The reaction proceeded well under transition-metal-free conditions and exhibited a wide substrate scope and functional group tolerance. The preliminary studies suggested that the nucleophilic sulfonyl sources were generated in situ via the reaction of CS₂, Et₂NH and sulfonyl chlorides.