Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide

BOUCHET, LYDIA; ALICIA B. PEÑÉÑORY; ARGÜELLO, JUAN E

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2011 vol. 52 p. 969 - 969

0040-4039

elenobenzamide (-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 electronwithdrawing substituents, such as nitro and carbonyl groups.