PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: Facile synthesis of β-acetoxysulfides

Charoensak Muangkaew; Praewpan Katrun; Patcharaphon Kanchanarugee; Manat Pohmakotr; Vichai Reutrakul; Darunee Soorukram; Thaworn Jaipetch; Chutima Kuhakarn

doi:10.1016/j.tet.2013.08.018

PhI(OAc)₂/KI mediated 1,2-acetoxysulfenylation of alkenes: Facile synthesis of β-acetoxysulfides

Charoensak Muangkaew
, Praewpan Katrun
, Patcharaphon Kanchanarugee
, Manat Pohmakotr
, Vichai Reutrakul
, Darunee Soorukram
, Thaworn Jaipetch
, Chutima Kuhakarn

Mahidol University
Mahidol University

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

49 Citations (Scopus)

Abstract

A convenient method for 1,2-acetoxysulfenylation of alkenes using disulfide promoted by (diacetoxyiodo)benzene (PhI(OAc)₂, DIB)/KI was developed. The reaction is highly regioselective for styrene derivatives while aliphatic alkenes lead to a mixture of two regioisomers.

Original language	English
Pages (from-to)	8847-8856
Number of pages	10
Journal	Tetrahedron
Volume	69
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2013.08.018
Publication status	Published - 21 Oct 2013
Externally published	Yes

Keywords

Acetoxysulfenylation
Acetoxysulfides
Oxidation
PhI(OAc)
Sulfides

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10.1016/j.tet.2013.08.018

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title = "PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: Facile synthesis of β-acetoxysulfides",

abstract = "A convenient method for 1,2-acetoxysulfenylation of alkenes using disulfide promoted by (diacetoxyiodo)benzene (PhI(OAc)2, DIB)/KI was developed. The reaction is highly regioselective for styrene derivatives while aliphatic alkenes lead to a mixture of two regioisomers.",

keywords = "Acetoxysulfenylation, Acetoxysulfides, Oxidation, PhI(OAc), Sulfides",

author = "Charoensak Muangkaew and Praewpan Katrun and Patcharaphon Kanchanarugee and Manat Pohmakotr and Vichai Reutrakul and Darunee Soorukram and Thaworn Jaipetch and Chutima Kuhakarn",

year = "2013",

month = oct,

day = "21",

doi = "10.1016/j.tet.2013.08.018",

language = "English",

volume = "69",

pages = "8847--8856",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "42",

}

TY - JOUR

T1 - PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes

T2 - Facile synthesis of β-acetoxysulfides

AU - Muangkaew, Charoensak

AU - Katrun, Praewpan

AU - Kanchanarugee, Patcharaphon

AU - Pohmakotr, Manat

AU - Reutrakul, Vichai

AU - Soorukram, Darunee

AU - Jaipetch, Thaworn

AU - Kuhakarn, Chutima

PY - 2013/10/21

Y1 - 2013/10/21

N2 - A convenient method for 1,2-acetoxysulfenylation of alkenes using disulfide promoted by (diacetoxyiodo)benzene (PhI(OAc)2, DIB)/KI was developed. The reaction is highly regioselective for styrene derivatives while aliphatic alkenes lead to a mixture of two regioisomers.

AB - A convenient method for 1,2-acetoxysulfenylation of alkenes using disulfide promoted by (diacetoxyiodo)benzene (PhI(OAc)2, DIB)/KI was developed. The reaction is highly regioselective for styrene derivatives while aliphatic alkenes lead to a mixture of two regioisomers.

KW - Acetoxysulfenylation

KW - Acetoxysulfides

KW - Oxidation

KW - PhI(OAc)

KW - Sulfides

UR - https://www.scopus.com/pages/publications/84883487957

U2 - 10.1016/j.tet.2013.08.018

DO - 10.1016/j.tet.2013.08.018

M3 - Article

AN - SCOPUS:84883487957

SN - 0040-4020

VL - 69

SP - 8847

EP - 8856

JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

PhI(OAc)₂/KI mediated 1,2-acetoxysulfenylation of alkenes: Facile synthesis of β-acetoxysulfides

Abstract

Keywords

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