139780-24-8Relevant academic research and scientific papers
Electrosynthesis of unsymmetrical donor-acceptor polyaryls
Boy,Combellas,Thiebault,Amatore,Jutand
, p. 491 - 494 (1992)
Unsymmetrical Donor-Acceptor Polyaryls are synthesized by an electrochemically induced SRN1 reaction using 2,6-ditertbutyl phenoxide as nucleophile and acceptor substituted polyarylbromides The latter are synthesized by a cross coupling reaction of aromatic organometallic reagents and aromatic halides catalyzed by palladium complexes.
Electrosynthesis of Unsymmetrical Polyaryls by a SRN1-Type Reaction
Boy, P.,Combellas, C.,Suba, C.,Thiebault, A.
, p. 4482 - 4489 (2007/10/02)
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.
