General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium

Article abstract of DOI:10.1016/S0040-4039(01)00820-6

Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a S_H2 mechanism via alkyl radicals.