One-pot synthetic method of unsymmetrical diorganyl selenides: reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal

A convenient synthetic method of unsymmetrical selenides has been developed. When diphenyl diselenide was allowed to react with two equimolar amounts of primary alkyl iodides and bromides in the presence of an equimolar amount of lanthanum metal, alkyl phenyl selenides were formed in moderate to good yields. For the reaction of primary alkyl chlorides and secondary alkyl iodides, the yields of the selenides were low; however, the yields were dramatically improved by the addition of TMEDA or HMPA. A reaction pathway involving the generation of a lanthanum phenylselenolate intermediate was suggested.