Copper-Catalyzed Defluorinative Boroarylation of Alkenes with Polyfluoroarenes

A catalytic defluorinative boroarylation of alkenes with polyfluoroarenes and B(2)pin(2) with the assistance of a PCy3-ligated copper catalyst was developed. Taking advantage of benchstable alkenes as latent nucleophiles and avoiding traditional reliance on stoichiometric quantities of organometallics, this method showcased good functional group compatibility and proceeded under very mild reaction conditions. A series of valuable boronate-containing polyfluoroarenes including all-carbon quaternary carboncenter-containing triaryl alkylboronates that are otherwise difficult to access were efficiently prepared.

Automated summary

A catalytic defluorinative boroarylation of alkenes with polyfluoroarenes and B(2)pin(2) was achieved using a PCy3-ligated copper catalyst. This method demonstrated good functional group compatibility and proceeded under mild reaction conditions, avoiding the need for stoichiometric quantities of organometallics. Valuable boronate-containing polyfluoroarenes, including challenging all-carbon quaternary carboncenter-containing triaryl alkylboronates, were efficiently synthesized.