Nucleophilic borylation of fluorobenzenes with reduced arylboranes

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 SNAr-type reactions on fluorobenzenes under mild conditions using Na-2[FluB=BFlu], Li-2[HBFlu], and Li-2[Me(2)DBA] (BFlu = 9-borafluorenyl, Me(2)DBA = 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene).