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Contents Vol 72(11)

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

Andrew Thomas Holm A , Sanatan Nayak A and Philip Wai Hong Chan A B C
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

B Department of Chemistry, University of Warwick, Coventry CV4 7AL, UK.

C Corresponding author. Email: phil.chan@monash.edu

Australian Journal of Chemistry 72(11) 881-889 https://doi.org/10.1071/CH19330
Submitted: 16 July 2019  Accepted: 27 August 2019   Published: 14 October 2019

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.


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