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Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides

Hui-Lan Yue, Martin Klussmann*

*Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45479 Mülheim an der Ruhr, Germany, Email:

H.-L. Yue, M. Klussmann, Synlett, 2016, 27, 2505-2509.

DOI: 10.1055/s-0035-1562480

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An oxidative variant of the thiol-ene reaction enables the direct addition of thiols to olefins to form sulfoxides in the presence of tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.

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Key Words

addition, homogeneous catalysis, oxygenations, TBHP, radical reaction, sulfoxides

ID: J60-Y2016