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Catalytic Electrophilic Halogenation of Silyl‐Protected and Terminal Alkynes: Trapping Gold(I) Acetylides

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Abstract:

Abstract

In the presence of a cationic gold(I) catalyst and N‐halosuccinimide, both trimethylsilyl‐protected and terminal alkynes are converted into alkynyl halides. Further experiments showed that silyl‐protected alkynes undergo electrophilic iodination and bromination under Brønsted acid catalysis, whilst terminal alkynes require a cationic gold catalyst. The former reactions probably proceed via activation of the electrophile, whilst the latter reactions proceed via a gold(I) acetylide intermediate. Gold‐catalysed halogenation was further combined with gold‐catalysed hydration and subsequent annulation to provide convenient routes to iodomethyl ketones and five‐membered aromatic heterocycles.

Document Type: Research Article

DOI: http://dx.doi.org/10.1002/adsc.201200491

Affiliations: Department of Chemistry, University College London, Christopher Ingold Laboratories, London WC1H 0AJ, U.K. phone: +(44)-(0)20-7679-2467, Fax: +(44)-(0)20-7679-7463

Publication date: November 26, 2012

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