Gold-Catalysed Oxidative Cycloisomerisation of 1,6-Diyne Acetates to 1-Naphthyl Ketones

Andrew Thomas Holm, Sanatan Nayak, Philip Wai Hong Chan

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3 Citations (Scopus)

Abstract

A synthetic method to prepare 1-naphthyl ketones from gold(i)-catalysed oxidative cycloisomerisation of 1,6-diyne acetates is described. The proposed mechanism involves cyclopropenation-cycloreversion of the 1,6-diyne motif initiated by a 1,2-acyloxy migration. This is followed by nucleophilic attack of the ensuing gold carbenoid species by a molecule of water and autoxidation to give the aromatic product.

Original languageEnglish
Pages (from-to)881-889
Number of pages9
JournalAustralian Journal of Chemistry
Volume72
Issue number11
DOIs
Publication statusPublished - 14 Oct 2019

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