Aryne, ortho-Quinone Methide, and ortho-Quinodimethane: Synthesis of Multisubstituted Arenes Using the Aromatic Reactive Intermediates

A useful synthetic method for building up multisubstituted arenes of structural complexity and diversity by use of aromatic reactive intermediates is described. Regardless of the transient character arising from a highly strained carbon carbon triple bond, arynes have been found to undergo facile insertion into an element element sigma-bond and three-component coupling reactions. In addition, ortho-quinone methides and ortho-quinodimethanes have also been demonstrated to be convertible into multisubstituted arenes by utilizing their exo-dienyl moieties.