Synlett 2013; 24(13): 1679-1682
DOI: 10.1055/s-0033-1339276
letter
© Georg Thieme Verlag Stuttgart · New York

Aerobic Oxidation of Sulfides with a Vitamin B2-Derived Organocatalyst

Yasushi Imada*
a   Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan   Fax: +81(6)68506222   eMail: naota@chem.es.osaka-u.ac.jp
b   Department of Chemical Science and Technology, Institute of Technology and Science, The University of Tokushima, Minamijosanjima 2-1, Tokushima 770-8506, Japan   Fax: +81(88)6567407   eMail: imada@chem.tokushima-u.ac.jp
,
Itoko Tonomura
a   Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan   Fax: +81(6)68506222   eMail: naota@chem.es.osaka-u.ac.jp
,
Naruyoshi Komiya
a   Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan   Fax: +81(6)68506222   eMail: naota@chem.es.osaka-u.ac.jp
,
Takeshi Naota*
a   Department of Chemistry, Graduate School of Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan   Fax: +81(6)68506222   eMail: naota@chem.es.osaka-u.ac.jp
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Publikationsverlauf

Received: 29. März 2013

Accepted after revision: 21. Mai 2013

Publikationsdatum:
28. Juni 2013 (online)


Abstract

5-Ethyl-3-methyl-2′,4′:3′,5′-di-O-methylenedioxy-riboflavinium perchlorate (DMRFlEt+ClO4 ) is readily derived from commercially available vitamin B2 (riboflavin) and exhibits high catalytic activity for the oxidation of organic sulfides under an oxygen atmosphere (1 atm) with the assistance of hydrazine hydrate as a reductant. This is an inexpensive, convenient, and environmentally benign method for the selective oxidative transformation of sulfides into sulfoxides.

Supporting Information

 
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