Electrosynthesis of Unsymmetrical Polyaryls by a SRN1-Type Reaction

Article abstract of DOI:10.1021/jo00095a024

Unsymmetrical polyaryls are electrosynthesized in liquid ammonia by a single-step S_RN1 reaction in the presence of a redox mediator starting from aromatic halides and 2,6-di-tert-butyl phenoxide.With monoaryl halides activated by electron-withdrawing substituents (N of pyridyl or quinolyl, trifluoromethyl, cyano, sulfone, ester, ketone, alkyl sulfide, N(1+) of anilinium), biaryls are obtained in good yields (between 50 and 95percent).The yields of ter- and quateraryls are lower (40percent maximum).The reaction is extended to other ortho-disubstituted phenols.Elimination reactions of the tert-butyl groups from the products are achieved by a Friedel-Crafts reaction using either trifluoromethanesulfonic acid or aluminum trichloride as catalysts.