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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 ?-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.

SUBMITTER: Hanson SS

PROVIDER: S-EPMC4581462 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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

Hanson Samuel S SS Doni Eswararao E Traboulsee Kyle T KT Coulthard Graeme G Murphy John A JA Dyker C Adam CA

Angewandte Chemie (International ed. in English) 20150724 38

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 pyridiniu ...[more]

PMID: 26213345

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Dataset Information

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

Publications

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

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