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

Praewpan Katrun; Teerawat Songsichan; Darunee Soorukram; Manat Pohmakotr; Vichai Reutrakul; Chutima Kuhakarn

doi:10.1055/s-0036-1588900

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

Praewpan Katrun
, Teerawat Songsichan
, Darunee Soorukram
, Manat Pohmakotr
, Vichai Reutrakul
, Chutima Kuhakarn

Mahidol University

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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.

Original language	English
Article number	ss-2016-n0517-op
Pages (from-to)	1109-1121
Number of pages	13
Journal	Synthesis (Germany)
Volume	49
Issue number	5
DOIs	https://doi.org/10.1055/s-0036-1588900
Publication status	Published - 1 Mar 2017
Externally published	Yes

Keywords

deacylation
iodine
o -iodoxybenzoic acid
sulfonylation
β-keto sulfone

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10.1055/s-0036-1588900

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

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.",

keywords = "deacylation, iodine, o -iodoxybenzoic acid, sulfonylation, β-keto sulfone",

author = "Praewpan Katrun and Teerawat Songsichan and Darunee Soorukram and Manat Pohmakotr and Vichai Reutrakul and Chutima Kuhakarn",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart · New York-Synthesis 2017.",

year = "2017",

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doi = "10.1055/s-0036-1588900",

language = "English",

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TY - JOUR

T1 - O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds

T2 - A Synthesis of β-Carbonyl Sulfones

AU - Katrun, Praewpan

AU - Songsichan, Teerawat

AU - Soorukram, Darunee

AU - Pohmakotr, Manat

AU - Reutrakul, Vichai

AU - Kuhakarn, Chutima

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart · New York-Synthesis 2017.

PY - 2017/3/1

Y1 - 2017/3/1

N2 - 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.

AB - 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.

KW - deacylation

KW - iodine

KW - o -iodoxybenzoic acid

KW - sulfonylation

KW - β-keto sulfone

UR - https://www.scopus.com/pages/publications/84992702665

U2 - 10.1055/s-0036-1588900

DO - 10.1055/s-0036-1588900

M3 - Article

AN - SCOPUS:84992702665

SN - 0039-7881

VL - 49

SP - 1109

EP - 1121

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 5

M1 - ss-2016-n0517-op

ER -

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

Abstract

Keywords

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