Rh(III)‐Catalyzed C−H Annulation of Sulfoxonium Ylides and 1,3‐Diynes: A Rapid Access to Alkynyl‐1‐Naphthol Derivatives

A highly efficient Rh(III)-catalyzed redox-neutral [4+2]-annulation of sulfoxonium ylides with 1,3-diynes is reported. The reaction proceeded under operationally simple conditions and furnishes diverse aryl-alkynyl substituted 1-naphthols, 3-alkynyl-1-naphthols and unsymmetrical binaphthols in moderate to high yields.

Abstract

An effective redox-neutral strategy to synthesize aryl/alkynyl and alkyl/alkynyl substituted 1-naphthol derivatives has been efficaciously developed by Rh(III)-catalyzed [4+2]-annulation of sulfoxonium ylides and 1,3-diynes with excellent regio- and chemoselectivity. Subsequently, the same strategy was extended to furnish various unsymmetrical binaphthol motifs in one-pot manner. Interestingly, the TMS-derived 1,3-diyne predominantly delivered the 3-alkynyl-1-naphthol via desilylation pathway. The salient features such as traceless directing group, broad substrate scope, good functional group tolerance, and operationally simple conditions made the present protocol more valuable and appealing.

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