Electrochemically catalyzed aromatic nucleophilic substitution. Phenoxide ion as nucleophile

…, C Amatore, C Combellas, J Pinson…

Index: Alam, Nayat; Amatore, Christian; Comballas, Catherine; Pinson, Jean; Saveant, Jean-Michel; et al. Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1496 - 1504

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Citation Number: 50

Abstract

Cyclic voltammetry and preparative-scale electrolysis of aryl halides in the presence of phenoxide ions, a nucleophile reputed as unreactive in Sml reactions, show the formation, in liquid ammonia or in dimethyl sulfoxide, of coupling products along an electrochemically catalyzed Sml aromatic substitution process. Coupling occurs at carbons of the phenyl ring rather than at the phenolic oxygen. The mechanism of the reaction is established on ...

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