A site-selective and stereospecific cascade Suzuki-Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2'-dihalo 1,1'-biaryls

Abstract

A cascade Suzuki-Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.