Nickel-Catalyzed Thiolation and Selenylation of Cycloketone Oxime Esters with Thiosulfonate or Seleniumsulfonate

A nickel-catalyzed ring opening and, subsequently, reductive cross-coupling of cycloketone oxime esters with thiosulfonate or seleniumsulfonate are reported, which involves C–C bond cleavage and C(sp 3 )–S or C(sp 3 )–Se bond formation. Notably, S -aryl/alkyl sulfonothioates and Se -alkyl seleniumsulfonothioates could be employed in this reaction to afford a variety of 1° and 2° alkyl sulfides, aryl sulfides, and 1° and 2° alkyl selenides in one step. This strategy features easily available substrates and mild reaction conditions.