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

Hanson SS, Doni E, Traboulsee KT, Coulthard G, Murphy JA, Dyker CA - Angew. Chem. Int. Ed. Engl. (2015)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada).

No MeSH data available.


The reduction of sulfonamides by in situ generated 1 (Ts=tosyl group and Ms=mesyl group).
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sch4: The reduction of sulfonamides by in situ generated 1 (Ts=tosyl group and Ms=mesyl group).


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

Hanson SS, Doni E, Traboulsee KT, Coulthard G, Murphy JA, Dyker CA - Angew. Chem. Int. Ed. Engl. (2015)

The reduction of sulfonamides by in situ generated 1 (Ts=tosyl group and Ms=mesyl group).
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4581462&req=5

sch4: The reduction of sulfonamides by in situ generated 1 (Ts=tosyl group and Ms=mesyl group).
Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3 (Canada).

No MeSH data available.