CeCl_3/Sm induced reductive cleavage of the S-S bond in disulfide:A novel method for the synthesis of beta-thioesters,thiol-esters and alkylphenyl sulfides

摘要

Disulfide has been reduced by cerium trichloride and samarium in tetrahydrofuran to produce samarium thiolates.The"living"species reacts smoothly with alpha,beta-unsaturated esters(nitriles)to afford beta-thioesters(nitrile)under mild and neutral conditions.The new thiolate anion also reacts with acyl halides,anhydrides and alkyl or benzyl halides to give thioesters and sulfides,respectively.