Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts

J.A. Murphy; J. Garnier; S.R. Park; F. Schoenebeck; S.Z. Zhou; A.T. Turner

doi:10.1021/ol800134g

Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts

J.A. Murphy, J. Garnier, S.R. Park, F. Schoenebeck, S.Z. Zhou, A.T. Turner

Pure And Applied Chemistry

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

103 Citations (Scopus)

Abstract

Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = −1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.

Original language	English
Pages (from-to)	1227-1230
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	6
DOIs	https://doi.org/10.1021/ol800134g
Publication status	Published - 20 Mar 2008

Keywords

super-electron donors
bis-pyridinylidene
pyridinium salts

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10.1021/ol800134g

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 = "Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts",

abstract = "Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = −1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.",

keywords = "super-electron donors, bis-pyridinylidene, pyridinium salts",

author = "J.A. Murphy and J. Garnier and S.R. Park and F. Schoenebeck and S.Z. Zhou and A.T. Turner",

year = "2008",

month = mar,

day = "20",

doi = "10.1021/ol800134g",

language = "English",

volume = "10",

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journal = "Organic Letters",

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T2 - bis-pyridinylidene formation by base treatment of pyridinium salts

AU - Murphy, J.A.

AU - Garnier, J.

AU - Park, S.R.

AU - Schoenebeck, F.

AU - Zhou, S.Z.

AU - Turner, A.T.

PY - 2008/3/20

Y1 - 2008/3/20

N2 - Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = −1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.

AB - Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = −1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.

KW - super-electron donors

KW - bis-pyridinylidene

KW - pyridinium salts

U2 - 10.1021/ol800134g

DO - 10.1021/ol800134g

M3 - Article

SN - 1523-7060

VL - 10

SP - 1227

EP - 1230

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts

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