Bis(pentafluorophenyl)borane catalyzed atom-economic formation of alkenyl- and (homo)allyl boronates from dienes and boronic esters

Abstract

Based on the finding that bis(pentafluorophenyl)borane reacts with dienes at elevated temperatures to alkenyl boranes, contrary to the expected alkyl boranes, we developed a scalable and atom-economic bis(pentafluorophenyl)borane-catalyzed process for the synthesis of alkenyl and (homo)allyl boronates from dienes and boronic esters. This method enables the synthesis of cyclic alkenyl boronates with normal ring size that were previously inaccessible via the catalyzed hydroboration of alkynes.