Silyloxymethylation of Aryl Halides via Metallaphotoredox Catalyzed Desulfinative Cross‐Coupling with Silyl Rongalite

Abstract

AbstractA visible‐light‐triggered silyloxymethylation of aryl halides has been developed by the merger of photoredox and transition metal catalysis. Under the Ru/Ni dual catalytic conditions, sodium tert‐butyl‐dimethylsilyloxymethanesulfinate (SOMS) undergoes facile extrusion of sulfur dioxide to engender a silyloxymethyl radical that engages in the cross‐coupling with a range of aryl halides to produce benzyl silyl ether derivatives. The protocol is also effective with alkenyl halides and triflates, thus offering an efficient synthetic approach to the silyl‐protected allylic alcohols.