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Super-electron donors : bis-pyridinylidene formation by base treatment of pyridinium salts

Murphy, J.A. and Garnier, J. and Park, S.R. and Schoenebeck, F. and Zhou, S.Z. and Turner, A.T. (2008) Super-electron donors : bis-pyridinylidene formation by base treatment of pyridinium salts. Organic Letters, 10 (6). pp. 1227-1230. ISSN 1523-7060

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Deprotonation of bispyridinium salt 7b affords bispyridinylidene 10, a very powerful neutral organic two-electron donor [E1/2 (DMF) = −1.13 V vs Ag/AgCl/KCl (sat)], presumably via the pyridinylidene 8. Donor 10 reduces aryl iodides and bromides to aryl anions in excellent yield and also reductively cleaves selected phenylalkylsulfones very efficiently.