Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 40, Pages 10755-10758Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405996
Keywords
benzyl halides; organocatalysis; stilbenes; sulfenate anions; sulfoxides
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Funding
- National Science Foundation [CHE-0848460, 1152488]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1152488] Funding Source: National Science Foundation
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Sulfenate anions are known to act as highly reactive species in the organic arena. Now they premiere as organo-catalysts. Proof of concept is offered by the sulfoxide/sulfenate-catalyzed (1-10 mol%) coupling of benzyl halides in the presence of base to generate trans-stilbenes in good to excellent yields (up to 99%). Mechanistic studies support the intermediacy of sulfenate anions, and the deprotonated sulfoxide was determined to be the resting state of the catalyst.
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