Synthesis 2012; 44(11): 1693-1699
DOI: 10.1055/s-0031-1290952
paper
© Georg Thieme Verlag Stuttgart · New York

IBX/I2-Mediated Reaction of Sodium Arenesulfinates with Alkenes: Facile Synthesis of β-Keto Sulfones

Natthapol Samakkanad
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Praewpan Katrun
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Thanachart Techajaroonjit
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Sornsiri Hlekhlai
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Manat Pohmakotr
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Vichai Reutrakul
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Thaworn Jaipetch
b   Mahidol University, Kanchanaburi Campus, Saiyok, Kanchanaburi 71150, Thailand
,
Darunee Soorukram
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
,
Chutima Kuhakarn*
a   Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand, Fax: +88(6)3547151   eMail: chutima.kon@mahidol.ac.th
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Publikationsverlauf

Received: 13. Februar 2012

Accepted after revision: 19. März 2012

Publikationsdatum:
27. April 2012 (online)


Abstract

A direct synthesis of β-keto sulfones from alkenes is described. A combination of o-iodoxybenzoic acid/iodine (IBX/I2) was found to mediate the reactions of alkenes with arenesulfinates to yield β-keto sulfones in good yields via a one-pot reaction.

 
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