Substituted naphthalenes and naphthols from benzynes and dienolate anions

Abstract

A direct method for the preparation of substituted naphthalenes and naphthols from benzynes and dienolate anions is described. The naphthols are thus formed from conjugated esters and the naphthalenes from conjugated ketones. The scope and mechanism of the reaction have been briefly explored. Reaction between the dienolate anion from mesityl oxide and the benzyne from 2-(or 3-)bromoanisole produces 8-methoxy-1,3-dimethylnaphthalene in a regioselective manner.