Theory and Experimental Illustration of Preparative Electrochemistry Using Redox Catalysis of Electron Transfer Initiated Radical Chain Reactions. Application to the Cross-Coupling between Aryl Halides and Phenoxide Ions

Article abstract of DOI:10.1021/jo00313a022

A general equation predicting the yield of electron transfer initiated radical chain reaction (S_RN1 and related mechanisms) under preparative electrochemical conditions is given for situations where the electron-transfer activation of the chain is performed by means of a redox mediator.Simple tests, allowing for the choice of proper redox mediator, are given, and their origins established and discussed.The validity and application of this simple model is shown and discussed for the case of the S_RN1-like reaction involving di-tert-butylphenoxide as a nucleophile, to afford biaryls of interest for their properties in nonlinear optics.