Sulfur-Arylation of Sulfenamides via Chan-Lam Coupling with Boronic Acids: Access to High Oxidation State Sulfur Pharmacophores

Sulfur-arylation of sulfenamides is reported. This reaction proceeds via a Chan-Lam-type coupling with commercially abundant boronic acids to give sulfilimines. A broad scope was established with a variety of readily accessible aryl and alkyl sulfenamide and boronic acid inputs. Synthetic utility and functional group compatibility were further demonstrated through the direct late-stage introduction of sulfilimines into approved drugs. Derivatization of the sulfilimine products provided access to medicinally relevant sulfoximines and sulfondiimines.

Automated summary

Sulfur-arylation of sulfenamides via a Chan-Lam-type coupling with boronic acids is reported, leading to the formation of sulfilimines. A broad range of aryl and alkyl sulfenamides and boronic acids were used as reactants. The utility of this reaction was demonstrated by introducing sulfilimines into approved drugs and accessing medicinally relevant sulfoximines and sulfondiimines through derivatization of sulfilimine products.