Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides

Eman Zawia; Wesley J. Moran

doi:10.3390/molecules21081073

Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides

Eman Zawia, Wesley J. Moran

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

9 Citations (Scopus)

Abstract

Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.

Original language	English
Article number	1073
Number of pages	11
Journal	Molecules
Volume	21
Issue number	8
DOIs	https://doi.org/10.3390/molecules21081073
Publication status	Published - 16 Aug 2016

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http://eprints.hud.ac.uk/id/eprint/29246/Licence: CC BY

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title = "Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides",

abstract = "Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.",

keywords = "Hypervalent iodine, Iodonium salt, Solvolysis, Substitution",

author = "Eman Zawia and Moran, {Wesley J.}",

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T1 - Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides

AU - Zawia, Eman

AU - Moran, Wesley J.

PY - 2016/8/16

Y1 - 2016/8/16

N2 - Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.

AB - Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides.

KW - Hypervalent iodine

KW - Iodonium salt

KW - Solvolysis

KW - Substitution

UR - http://www.scopus.com/inward/record.url?scp=84983343763&partnerID=8YFLogxK

U2 - 10.3390/molecules21081073

DO - 10.3390/molecules21081073

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JO - Molecules

JF - Molecules

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ER -

Aqueous DMSO mediated conversion of (2-(arylsulfonyl)vinyl)iodonium salts to aldehydes and vinyl chlorides

Abstract

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