Reductive cleavage of sulfones and sulfonamides by neutral organic super electron-donor (S.E.D.) reagent

Fransziska Schoenebeck; John A. Murphy; Sheng-ze Zhou; Yoshitaka Uenoyama; Yves Miclo; Tell Tuttle

doi:10.1021/ja074417h

Reductive cleavage of sulfones and sulfonamides by neutral organic super electron-donor (S.E.D.) reagent

Fransziska Schoenebeck, John A. Murphy, Sheng-ze Zhou, Yoshitaka Uenoyama, Yves Miclo, Tell Tuttle

Pure And Applied Chemistry

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Abstract

The sulfonyl group finds extensive applications in organic and medicinal chemistry both in sulfonamides, popular as robust protecting groups for amines, and in sulfones. Frequently, sulfones are introduced into synthetic schemes to assist particular transformations; further progress along the synthetic route can later require the removal of a sulfone group, and this can be achieved by reductive desulfonylation or, in the special cases of α-halo- or ß-acyloxysulfones, by elimination to an alkene.

Original language	English
Pages (from-to)	13368-13369
Number of pages	1
Journal	Journal of American Chemical Society
Volume	129
Issue number	44
DOIs	https://doi.org/10.1021/ja074417h
Publication status	Published - 16 Oct 2007

Keywords

super electron donor
sulfonamides
sulfones

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10.1021/ja074417h

329036.pdfFinal published version, 50.8 KB

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)
Murphy, J. (Principal Investigator), Coombs, G. (Co-investigator), Ferguson, A. (Co-investigator) & Florence, A. (Co-investigator)
Scottish Funding Council SFC, EPSRC (Engineering and Physical Sciences Research Council)
1/09/07 → 30/10/12
Project: Research
New horizons in organic electron transfer
Murphy, J. (Principal Investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/10/06 → 30/09/09
Project: Research

Cite this

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title = "Reductive cleavage of sulfones and sulfonamides by neutral organic super electron-donor (S.E.D.) reagent",

abstract = "The sulfonyl group finds extensive applications in organic and medicinal chemistry both in sulfonamides, popular as robust protecting groups for amines, and in sulfones. Frequently, sulfones are introduced into synthetic schemes to assist particular transformations; further progress along the synthetic route can later require the removal of a sulfone group, and this can be achieved by reductive desulfonylation or, in the special cases of α-halo- or {\ss}-acyloxysulfones, by elimination to an alkene.",

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T1 - Reductive cleavage of sulfones and sulfonamides by neutral organic super electron-donor (S.E.D.) reagent

AU - Schoenebeck, Fransziska

AU - Murphy, John A.

AU - Zhou, Sheng-ze

AU - Uenoyama, Yoshitaka

AU - Miclo, Yves

AU - Tuttle, Tell

PY - 2007/10/16

Y1 - 2007/10/16

N2 - The sulfonyl group finds extensive applications in organic and medicinal chemistry both in sulfonamides, popular as robust protecting groups for amines, and in sulfones. Frequently, sulfones are introduced into synthetic schemes to assist particular transformations; further progress along the synthetic route can later require the removal of a sulfone group, and this can be achieved by reductive desulfonylation or, in the special cases of α-halo- or ß-acyloxysulfones, by elimination to an alkene.

AB - The sulfonyl group finds extensive applications in organic and medicinal chemistry both in sulfonamides, popular as robust protecting groups for amines, and in sulfones. Frequently, sulfones are introduced into synthetic schemes to assist particular transformations; further progress along the synthetic route can later require the removal of a sulfone group, and this can be achieved by reductive desulfonylation or, in the special cases of α-halo- or ß-acyloxysulfones, by elimination to an alkene.

KW - super electron donor

KW - sulfonamides

KW - sulfones

U2 - 10.1021/ja074417h

DO - 10.1021/ja074417h

M3 - Article

SN - 0002-7863

VL - 129

SP - 13368

EP - 13369

JO - Journal of American Chemical Society

JF - Journal of American Chemical Society

IS - 44

ER -

Reductive cleavage of sulfones and sulfonamides by neutral organic super electron-donor (S.E.D.) reagent

Abstract

Keywords

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Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

New horizons in organic electron transfer

Cite this