Synthesis of 1-arylnaphthalenes by gold-catalyzed one-pot sequential epoxide to carbonyl rearrangement and cyclization with arylalkynes

Abstract

Intermolecular and intramolecular reactions of a one-pot gold-catalyzed epoxide rearrangement followed by an electrophilic addition to arylalkynes to synthesize 1-arylnaphthalenes have been reported. The intramolecular reaction has been applied to synthesize 1-arylnaphthalenes fused with saturated furan, pyran, pyrrole, and cyclopentane ring systems. A gold-catalyzed regioselective one-pot synthesis of 1-arylnaphthalenes from aryl epoxides has been presented. Both intermolecular and intramolecular cyclizations have been demonstrated. The intramolecular reactions provided 1-arylnaphthalenes fused with saturated furan/pyran/pyrrole/cyclopentane ring systems. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.