Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)‐Substituted Bispyridinylidene

E-ISSN： 1521-3757|127|38|11388-11391

ISSN： 0044-8249

Source： ANGEWANDTE CHEMIE, Vol.127, Iss.38, 2015-09, pp. : 11388-11391

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

Previous Menu Next

Abstract

AbstractA 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N bond cleavage of N,N‐dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.