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

Selenobenzamide (−SeCNH(Ph), 1), selenourea (−SeCNH(NH2), 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.