Se-(Fluoromethyl) Benzenesulfonoselenoates: Shelf-Stable, Easily Available Reagents for Monofluoromethylselenolation

A new class of electrophilic monofluoromethylselenolation reagents, Se-(fluoromethyl) benzenesulfonoselenoates, has been developed. They can be readily prepared from sodium benzenesulfinates, Se powder and ClCFH2 in one step under mild reaction conditions. Se-(fluoromethyl) benzenesulfonoselenoates are efficient electrophilic monofluoromethylselenolation reagents for a wide range of nucleophiles including indole, 6-azaindole, pyrrole, thiophene, electron-rich arene, aryl boronic acid and alkyne. The monofluoromethylselenolation approach features mild and environmentally friendly reaction conditions, good tolerance of various functional groups, and broad substrate scope.

Automated summary

A new class of electrophilic monofluoromethylselenolation reagents have been developed, which can be easily prepared in one step under mild reaction conditions. These reagents exhibit efficient electrophilic monofluoromethylselenolation reactions towards various nucleophiles, with mild and environmentally friendly reaction conditions, good tolerance of functional groups, and broad substrate scope.