Synthesis 2017; 49(05): 1109-1121
DOI: 10.1055/s-0036-1588900
paper
© Georg Thieme Verlag Stuttgart · New York

o-Iodoxybenzoic Acid (IBX)–Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones

Praewpan Katrun
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand   Email: chutima.kon@mahidol.ac.th
,
Teerawat Songsichan
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand   Email: chutima.kon@mahidol.ac.th
,
Darunee Soorukram
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand   Email: chutima.kon@mahidol.ac.th
,
Manat Pohmakotr
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand   Email: chutima.kon@mahidol.ac.th
,
Vichai Reutrakul
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand   Email: chutima.kon@mahidol.ac.th
,
Chutima Kuhakarn*
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand   Email: chutima.kon@mahidol.ac.th
› Author Affiliations
Further Information

Publication History

Received: 22 July 2016

Accepted after revision: 28 September 2016

Publication Date:
26 October 2016 (online)


Abstract

A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.

Supporting Information