A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.

Automated summary

A new air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction for the synthesis of diaryl sulfones has been developed, tolerating a wide range of polar functional groups. Control experiments and DFT calculations elucidated the mechanism involving the formation of a Cu(I)-sulfinate intermediate through fast insertion of a SO2 molecule.