Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 15, Pages 3854-3858Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310280
Keywords
acetylides; alkynes; cyclization; gold; vinylidenes
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Funding
- Fonds der Chemischen Industrie
- Alexander von Humboldt foundation
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Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the -carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold-catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross-coupling reactions, for example.
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