Generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super electron donor (SED)

Murphy, J.A. and Zhou, S. and Tuttle, C.T. and Schoenebeck, F. and Mohan, M. and Park, S.R. and Berlouis, L.E.A. and Thomson, D.W. (2007) Generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super electron donor (SED). Agewandte Chemie-International Edition, 46. pp. 5178-5183. ISSN 1433-7851 (http://dx.doi.org/10.1002/anie.200700554)

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Abstract

Stabilized carbanions can be prepared by deprotonation of the corresponding carbon acids, but more reactive carbanions, such as aryl anions, are usually made by metal–halogen exchange or by electrochemical routes.[1] Whereas the use of metals and organometallic compounds to form aryl anions is well established, the use of totally organic electron-transfer agents, in the absence of photochemical activation, is completely unknown.[2] Herein we report the first neutral organic molecule to achieve this feat.

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