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

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Hanson, Samuel S. and Doni, Eswararao and Traboulsee, Kyle T. and Coulthard, Graeme and Murphy, John A. and Dyker, C. Adam (2015) Pushing the limits of neutral organic electron donors : A tetra(iminophosphorano)-substituted bispyridinylidene. Angewandte Chemie International Edition, 54 (38). pp. 11236-11239. ISSN 1521-3773 (https://doi.org/10.1002/anie.201505378)

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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.

ORCID iDs

Hanson, Samuel S., Doni, Eswararao, Traboulsee, Kyle T., Coulthard, Graeme ORCID logoORCID: https://orcid.org/0000-0002-4413-2828, Murphy, John A. and Dyker, C. Adam;
CORE (COnnecting REpositories)