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

Yue, H.-L., & Klussmann, M. (2016). Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides. Synlett, 27(20), 2505-2509. doi:10.1055/s-0035-1562480.

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 Creators:
Yue , Hui-Lan1, Author
Klussmann, Martin1, Author              
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              

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Free keywords: addition - homogeneous catalysis - oxygenations - peroxides - radical reaction - sulfoxides
 Abstract: An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses 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. No special precautions are necessary to exclude oxygen, yet the products are formed without oxidation at the β-position. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.

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 Dates: 2016-06-25
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-0035-1562480
 Degree: -

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Title: Synlett
  Other : Synlett
Source Genre: Journal
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Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: 5 Volume / Issue: 27 (20) Sequence Number: - Start / End Page: 2505 - 2509 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856
DOI: 10.1055/s-0035-1562480