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Hydrothiolation of Alkenes and Alkynes Catalyzed by 3,4‐Dimethyl‐5‐vinylthiazolium iodide and Poly(3,4‐dimethyl‐5‐vinylthiazolium) iodide
Author(s) -
Chun Supill,
Chung Junyong,
Park Ji Eun,
Chung Young Keun
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600363
Subject(s) - iodide , chemistry , catalysis , markovnikov's rule , thiol , methyl iodide , organic chemistry , base (topology) , medicinal chemistry , polymer chemistry , photochemistry , regioselectivity , mathematical analysis , mathematics
The highly selective anti‐Markovnikov addition of thiols to unactivated alkenes and alkynes was demonstrated by using 3,4‐dimethyl‐5‐vinylthiazolium iodide or its polymer, poly(3,4‐dimethyl‐5‐vinylthiazolium) iodide, as a complementary catalyst. The reaction proceeded cleanly under base‐free conditions in air with both aromatic and aliphatic thiols. The polymer catalyst showed a high turnover number (≈5800) and could be reused up to four times without any loss of catalytic activity. DFT calculations supported stabilization of the thiyl radical intermediate by the thiazolium cation, which resulted in reaction of the radical with unsaturated C−C bonds.