Premium
A New Class of Organocatalysts: Sulfenate Anions
Author(s) -
Zhang Mengnan,
Jia Tiezheng,
Yin Haolin,
Carroll Patrick J.,
Schelter Eric J.,
Walsh Patrick J.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201405996
Subject(s) - deprotonation , sulfoxide , halide , catalysis , chemistry , coupling (piping) , base (topology) , class (philosophy) , medicinal chemistry , polymer chemistry , combinatorial chemistry , organic chemistry , materials science , ion , philosophy , mathematics , mathematical analysis , metallurgy , epistemology
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.