Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearrangement, are presented. The strategy involves introducing triallylborane prepared in situ in the allylation step. Moreover, a novel expedient method for the preparation of 9,10-diallylphenanthrene was introduced.
Keywords: Wagner-Meerwein rearrangement; allylation; metathesis; orthoquinones; pinacol rearrangement; polycyclic aromatic compounds (PACs); tris(pentafluorophenyl)borane.