title: A new class of organocatalysts: sulfenate anions.
abstract: 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 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.
authors.affiliation: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 S. 34thSt., Philadelphia, PA 19104-6323 (USA) https://sites.google.com/site/titaniumupenn/
authors.forename: Mengnan
authors.initials: M
authors.lastname: Zhang
authors.forename: Tiezheng
authors.initials: T
authors.lastname: Jia
authors.forename: Haolin
authors.initials: H
authors.lastname: Yin
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Eric J
authors.initials: EJ
authors.lastname: Schelter
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000838:Anions / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D006219:Halogens / Q000737:chemistry; D008958:Models, Molecular; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry; D013434:Sulfenic Acids / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000838:Anions; D001593:Benzyl Compounds; D006219:Halogens; D013267:Stilbenes; D013434:Sulfenic Acids; D013454:Sulfoxides
keywords: benzyl halides; organocatalysis; stilbenes; sulfenate anions; sulfoxides