Journal of Organic Chemistry p. 4482 - 4489 (1994)
Update date:2022-08-05
Topics:
Boy, P.
Combellas, C.
Suba, C.
Thiebault, A.
Unsymmetrical polyaryls are electrosynthesized in liquid ammonia by a single-step SRN1 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.
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