Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

Vittorio Pace; Laura Castoldi; Wolfgang Holzer

doi:10.1016/j.tetlet.2011.12.046

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

Vittorio Pace (Corresponding author), Laura Castoldi, Wolfgang Holzer

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.

Original language	English
Pages (from-to)	967-972
Number of pages	6
Journal	Tetrahedron Letters
Volume	53
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2011.12.046
Publication status	Published - 2012

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry

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10.1016/j.tetlet.2011.12.046

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title = "Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides",

abstract = "A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.",

author = "Vittorio Pace and Laura Castoldi and Wolfgang Holzer",

year = "2012",

doi = "10.1016/j.tetlet.2011.12.046",

language = "English",

volume = "53",

pages = "967--972",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "8",

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T1 - Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

AU - Pace, Vittorio

AU - Castoldi, Laura

AU - Holzer, Wolfgang

PY - 2012

Y1 - 2012

N2 - A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.

AB - A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.

U2 - 10.1016/j.tetlet.2011.12.046

DO - 10.1016/j.tetlet.2011.12.046

M3 - Article

SN - 0040-4039

VL - 53

SP - 967

EP - 972

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

Abstract

Austrian Fields of Science 2012

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