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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.
|Number of pages||4|
|Journal||Angewandte Chemie International Edition|
|Early online date||23 Jul 2015|
|Publication status||Published - 14 Sep 2015|
- electron transfer
- organic reductants
- substituent effects
FingerprintDive into the research topics of 'Pushing the limits of neutral organic electron donors: A tetra(iminophosphorano)-substituted bispyridinylidene'. Together they form a unique fingerprint.
- 1 Finished
Light-Activated Approaches to Highly Challenging Organic Electron Transfer Reactions
Murphy, J. & Zhou, S.
EPSRC (Engineering and Physical Sciences Research Council)
1/07/13 → 30/06/15