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

Research output: Contribution to journalArticle

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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.
LanguageEnglish
Pages1227-1230
Number of pages4
JournalOrganic Letters
Volume10
Issue number6
DOIs
Publication statusPublished - 20 Mar 2008

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Deprotonation
Iodides
Bromides
iodides
Anions
bromides
Salts
Electrons
anions
salts
electrons

Keywords

  • super-electron donors
  • bis-pyridinylidene
  • pyridinium salts

Cite this

Murphy, J. A., Garnier, J., Park, S. R., Schoenebeck, F., Zhou, S. Z., & Turner, A. T. (2008). Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts. Organic Letters, 10(6), 1227-1230. https://doi.org/10.1021/ol800134g
Murphy, J.A. ; Garnier, J. ; Park, S.R. ; Schoenebeck, F. ; Zhou, S.Z. ; Turner, A.T. / Super-electron donors : bis-pyridinylidene formation by base treatment of pyridinium salts. In: Organic Letters. 2008 ; Vol. 10, No. 6. pp. 1227-1230.
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Murphy, JA, Garnier, J, Park, SR, Schoenebeck, F, Zhou, SZ & Turner, AT 2008, 'Super-electron donors: bis-pyridinylidene formation by base treatment of pyridinium salts' Organic Letters, vol. 10, no. 6, pp. 1227-1230. https://doi.org/10.1021/ol800134g

Super-electron donors : bis-pyridinylidene formation by base treatment of pyridinium salts. / Murphy, J.A.; Garnier, J.; Park, S.R.; Schoenebeck, F.; Zhou, S.Z.; Turner, A.T.

In: Organic Letters, Vol. 10, No. 6, 20.03.2008, p. 1227-1230.

Research output: Contribution to journalArticle

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T2 - Organic Letters

AU - Murphy, J.A.

AU - Garnier, J.

AU - Park, S.R.

AU - Schoenebeck, F.

AU - Zhou, S.Z.

AU - Turner, A.T.

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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

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SP - 1227

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