Nucleophilic borylation of fluorobenzenes with reduced arylboranes

Abstract

Two challenging but rewarding topics in chemical synthesis are C–F-bond activation and the development of B-centered nucleophiles. We have now tackled both subjects simultaneously by forming aryl–B bonds via S_NAr-type reactions on fluorobenzenes under mild conditions using Na₂[FluBBFlu], Li₂[HBFlu], and Li₂[Me₂DBA] (BFlu = 9-borafluorenyl, Me₂DBA = 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene).