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

62 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 languageEnglish
Pages (from-to)1227-1230
Number of pages4
JournalOrganic Letters
Volume10
Issue number6
DOIs
Publication statusPublished - 20 Mar 2008

Keywords

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

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