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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405996
Subject(s) - deprotonation , sulfoxide , chemistry , halide , catalysis , polymer chemistry , organic chemistry , ion
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.