A new class of organocatalysts: sulfenate anions

Mengnan Zhang; Tiezheng Jia; Haolin Yin; Patrick J Carroll; Eric J Schelter; Patrick J Walsh

doi:10.1002/anie.201405996

A new class of organocatalysts: sulfenate anions

Angew Chem Int Ed Engl. 2014 Sep 26;53(40):10755-8. doi: 10.1002/anie.201405996. Epub 2014 Aug 11.

Authors

Mengnan Zhang¹, Tiezheng Jia, Haolin Yin, Patrick J Carroll, Eric J Schelter, Patrick J Walsh

Affiliation

¹ 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/

PMID: 25111259
DOI: 10.1002/anie.201405996

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.

Keywords: benzyl halides; organocatalysis; stilbenes; sulfenate anions; sulfoxides.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Anions / chemistry*
Benzyl Compounds / chemistry*
Catalysis
Halogens / chemistry
Models, Molecular
Stilbenes / chemical synthesis*
Stilbenes / chemistry
Sulfenic Acids / chemistry*
Sulfoxides / chemistry*

Substances

Anions
Benzyl Compounds
Halogens
Stilbenes
Sulfenic Acids
Sulfoxides