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Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)‐Substituted Bispyridinylidene
Author(s) -
Hanson Samuel S.,
Doni Eswararao,
Traboulsee Kyle T.,
Coulthard Graeme,
Murphy John A.,
Dyker C. Adam
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505378
Subject(s) - dication , chemistry , redox , saturated calomel electrode , cyclic voltammetry , pyridinium , photochemistry , tetra , deprotonation , aryl , electron donor , halide , inorganic chemistry , medicinal chemistry , ion , electrochemistry , electrode , organic chemistry , alkyl , working electrode , catalysis
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 SN bond cleavage of N , N ‐dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.
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