Synthesis of polyphenyls

A facile synthetic route toward functionalized 3-aryl-, 3,3′-diaryl-, 3,3′,5-triaryl-4,4′-dimethoxybiphenyls (polyphenyls) 3–5 with the terphenyl, quaterphenyl, quinquephenyl, and sexiphenyl skeleton starting from biphenyl-4,4′-diol (1) in modest total yield is described. The route has been carried by the two transformations of the regioselective NBS (N-bromosuccinimide)-mediated bromination of 2 in MeCN at reflux and Suzuki–Miyaura cross-coupling reaction of the resulting bromides with arylboronic acids 6 in DME at reflux.