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

Authors

  • 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
Weitere Informationen

Publikationsverlauf

Received: 22. Juli 2016

Accepted after revision: 28. September 2016

Publikationsdatum:
26. Oktober 2016 (online)


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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