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Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: trapping gold(I) acetylides vs. a bronsted acid-promoted reaction

Starkov, P; Rota, F; D'Oyley, JM; Sheppard, TD; (2012) Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: trapping gold(I) acetylides vs. a bronsted acid-promoted reaction. Advanced Synthesis & Catalysis , 354 (17) 3217 - 3224. 10.1002/adsc.201200491. Green open access

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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.

Type:Article
Title:Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: trapping gold(I) acetylides vs. a bronsted acid-promoted reaction
Open access status:An open access version is available from UCL Discovery
DOI:10.1002/adsc.201200491
Publisher version:http://dx.doi.org/10.1002/adsc.201200491
Language:English
Additional information:This is the peer reviewed version of the following article: Starkov, P; Rota, F; D'Oyley, JM; Sheppard, TD; (2012) Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: trapping gold(I) acetylides vs. a bronsted acid-promoted reaction. Advanced Synthesis & Catalysis , 354 (17) 3217 - 3224., which has been published in final form at http://dx.doi.org/10.1002/adsc.201200491. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving
Keywords:Alkynes, Bronsted acids, electrophilic halogenation, gold, haloalkynes, heterocycles
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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