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.
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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 UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/1369895 |
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