Al(2)O(3)-supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides

Abstract

Alumina-supported copper sulfate efficiently catalyzes electrophilic substitution in organoborane, organosilanes, and organostannanes by phenylselenium bromide providing a novel and efficient route to the synthesis of unsymmetrical diaryl and alkyl aryl selenides. A series of aryl, alkyl, and heteroaryl phenyl selenides were obtained in high yields. The catalyst is inexpensive, eco- and user-friendly, and recyclable. The mechanism involving Cu-assisted nucleophilic displacement of Br in PhSeBr by mild nucleophiles is described.