title: Pushing the limits of neutral organic electron donors: a tetra(iminophosphorano)-substituted bispyridinylidene.
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N bond cleavage of N,N-dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.
authors.affiliation: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada).
authors.forename: Samuel S
authors.initials: SS
authors.lastname: Hanson
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK).
authors.forename: Eswararao
authors.initials: E
authors.lastname: Doni
authors.affiliation: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada).
authors.forename: Kyle T
authors.initials: KT
authors.lastname: Traboulsee
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK).
authors.forename: Graeme
authors.initials: G
authors.lastname: Coulthard
authors.affiliation: WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL (UK). john.murphy@strath.ac.uk.
authors.forename: John A
authors.initials: JA
authors.lastname: Murphy
authors.affiliation: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada). cadyker@unb.ca.
authors.forename: C Adam
authors.initials: CA
authors.lastname: Dyker
keywords: electron transfer; iminophosphoranes; organic reductants; reduction; substituent effects