Synthesis of alkynyl and vinyl selenides via selenodecarboxylation of arylpropiolic and cinnamic acids

Abstract

The selenodecarboxylation of phenylpropiolic and cinnamic acid derivatives with diorgano diselenide is promoted by iodosobenzene diacetate (PhI(OAc) 2, IBDA) in acetonitrile at 30-60°C, leading to the formation of alkynyl selenides and vinyl selenides in moderate to excellent yields. Similar reactivity is also shown by iodosylbenzene (PhIO, IB). The reaction is also triggered in the solid state. An electrophilic mechanism is proposed for the transformation. © 2005 American Chemical Society.