Pushing the limits of neutral organic electron donors: A tetra(iminophosphorano)-substituted bispyridinylidene

Samuel S. Hanson, Eswararao Doni, Kyle T. Traboulsee, Graeme Coulthard, John A. Murphy, C. Adam Dyker

Research output: Contribution to journalArticle

42 Citations (Scopus)
111 Downloads (Pure)

Abstract

A new ground-state organic electron donor has been prepared that features four strongly π-donating iminophosphorano substituents on a bispyridinylidene skeleton. Cyclic voltammetry reveals a record redox potential of −1.70 V vs. saturated calomel electrode (SCE) for the couple involving the neutral organic donor and its dication. This highly reducing organic compound can be isolated (44 %) or more conveniently generated in situ by a deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive S[BOND]N bond cleavage of N,N-dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.
Original languageEnglish
Pages (from-to)11236-11239
Number of pages4
JournalAngewandte Chemie International Edition
Volume54
Issue number38
Early online date23 Jul 2015
DOIs
Publication statusPublished - 14 Sep 2015

    Fingerprint

Keywords

  • electron transfer
  • iminophosphoranes
  • organic reductants
  • reduction
  • substituent effects

Cite this