Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides

Abstract Selenobenzamide ( − SeCNH(Ph), 1 ), selenourea ( − SeCNH(NH 2 ), 2 ) and selenocyanate ( − SeCN, 3 ) anions afford areneselenolate ions (ArSe − ) under photostimulation in the presence of tert -butoxide or 2-naphthoxide ions as electron donors (entrainment conditions) in DMSO. In a ‘one-pot’ procedure, ArSe − anions can be trapped by a subsequent aliphatic nucleophilic substitution giving aryl methyl selenides in good to excellent yields (67–100%). This simple approach is compatible with electron-donating and electron-withdrawing substituents, such as nitro and carbonyl groups.