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

Org Lett. 2008 Mar 20;10(6):1227-30. doi: 10.1021/ol800134g. Epub 2008 Feb 21.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Electrochemistry
  • Electrons
  • Magnetic Resonance Spectroscopy
  • Pyridinium Compounds / chemistry*

Substances

  • Pyridinium Compounds