Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate

Article abstract of DOI:10.1016/j.tet.2006.03.039

A selective metal-halogen exchange/electrophilic quench protocol on 4,4′-dibromobiphenyl 4 that proceeds under non-cryogenic conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor.