SYNTHESIS OF BIS(ALKYLTHIO)BIPYRIDYLS BY NICKEL MEDIATED HOMO COUPLING OF HALOGENOPYRIDYL ALKYL SULPHIDES

Article abstract of DOI:10.1016/S0040-4020(01)80114-9

The homo coupling of some halogenopyridyl t-butyl sulphides with Ni(O) complex, formed in situ from nickel(II) chloride, triphenylphosphine and zinc dust in DMF, afforded bis(t-butylthio)bipyridyls in moderate to good yield.These compounds were dealkylated by electron transfer with sodium in HMPA; the resulting thiolate anions were directly treated with methyl iodide and the bis(methylthio)bipyridyls were obtained.The dealkylation with a solution of sodium in HMPA afforded the mono anions which, after treatment with methyl iodide, gave the t-butylthio(methylthio)bipyridyls.