Gold Catalysis of Non-Conjugated Haloacetylenes

Abstract

Gold-catalyzed reactions of conjugated haloacetylenes are well known and usually result in the formation of addition or dimerization products. Herein, we report a gold-catalyzed reaction of non-conjugated­ haloacetylenes, which leads exclusively to the halogenated cyclization products. Remarkable is the gold-catalyzed reaction of tritylhaloacetylenes to haloindene derivatives, as mechanistic studies reveal that an 1,2-aryl shift occurs in the initially formed gold complex. The potential functionalization at the halogen atom and the wide scope of these cyclization reactions make them an attractive method for the construction of cyclic systems.

Key words

gold catalysis - haloacetylenes - indene - chromene - chromane - 1,2-aryl shift - cyclization

Publication History

Received: 28 July 2020

Accepted after revision: 21 October 2020

Article published online:
26 November 2020

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