Electrochemically induced srn1 substitution in acetonitrile. Synthesis of arenes substituted by phenylseleno- and phenyltelluro groups

Article abstract of DOI:10.1016/S0040-4020(01)87831-5

In MeCN, the direct or mediated cathodic reduction of unactivated ArBr (Ar = 4-biphenyl, 2-fluorenyl, 9-anthryl) in the presence of an equivalent of PhE- (E = Se, Te) leads to ArEPh in interesting isolated yields (53-74 %) by S_NR1 substitution. The electrochemical synthesis of 9-phenylchalcogenoanthracene proceeds in better yields in MeCN than in DMSO. The 4,4′-disubstituted biphenyl PhSeC₆H₄C₆H₄SePh was prepared in 46 % yield in MeCN whereas its synthesis by photostimulation in liquid ammonia failed.