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

Andrew Thomas Holm; Sanatan Nayak; Philip Wai Hong Chan

doi:10.1071/CH19330

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

Andrew Thomas Holm, Sanatan Nayak, Philip Wai Hong Chan

School of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

1 Citation (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 language	English
Pages (from-to)	881-889
Number of pages	9
Journal	Australian Journal of Chemistry
Volume	72
Issue number	11
DOIs	https://doi.org/10.1071/CH19330
Publication status	Published - 14 Oct 2019

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10.1071/CH19330

291186402-oaFinal published version, 581 KB

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

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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AU - Chan, Philip Wai Hong

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Y1 - 2019/10/14

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

Abstract

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New Efficient Alkyne Cyclization Strategies for Complex Molecule Synthesis

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

Abstract

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New Efficient Alkyne Cyclization Strategies for Complex Molecule Synthesis

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