Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

Yuexia Zhang; Zeng Rong Wong; Xingxing Wu; Sherman J.L. Lauw; Xuan Huang; Richard D. Webster; Yonggui Robin Chi

doi:10.1039/C6CC08631D

Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

Yuexia Zhang, Zeng Rong Wong, Xingxing Wu, Sherman J.L. Lauw, Xuan Huang, Richard D. Webster, Yonggui Robin Chi^*

^*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.

Original language	English
Pages (from-to)	184-187
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	1
DOIs	https://doi.org/10.1039/C6CC08631D
Publication status	Published - 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/C6CC08631D

Cite this

@article{2038196cf5114af1b2c2645729b23c8b,

title = "Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant",

abstract = "Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.",

author = "Yuexia Zhang and Wong, {Zeng Rong} and Xingxing Wu and Lauw, {Sherman J.L.} and Xuan Huang and Webster, {Richard D.} and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/C6CC08631D",

language = "English",

volume = "53",

pages = "184--187",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "1",

}

TY - JOUR

T1 - Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

AU - Zhang, Yuexia

AU - Wong, Zeng Rong

AU - Wu, Xingxing

AU - Lauw, Sherman J.L.

AU - Huang, Xuan

AU - Webster, Richard D.

AU - Chi, Yonggui Robin

PY - 2017

Y1 - 2017

N2 - Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.

AB - Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.

UR - http://www.scopus.com/inward/record.url?scp=85006925445&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85006925445&partnerID=8YFLogxK

U2 - 10.1039/C6CC08631D

DO - 10.1039/C6CC08631D

M3 - Article

AN - SCOPUS:85006925445

SN - 1359-7345

VL - 53

SP - 184

EP - 187

JO - Chemical Communications

JF - Chemical Communications

IS - 1

ER -

Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this