A New Class of Organocatalysts: Sulfenate Anions1. Issue 40 (11th August 2014)

• Record Type: Journal Article
• Authors: Zhang, Mengnan; Jia, Tiezheng; Yin, Haolin; Carroll, Patrick J.; Schelter, Eric J.; Walsh, Patrick J.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 40(2014)
• Page Start: 10755
• Page End: 10758
• Publication Date: 2014-08-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405996
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Sulfenate anions are known to act as highly reactive species in the organic arena. Now they premiere as organocatalysts. Proof of concept is offered by the sulfoxide/sulfenate‐catalyzed (1–10 mol %) coupling of benzyl halides in the presence of base to generate <italic>trans</italic>‐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.</p> </abstract>