Al2O3-supported Cu-catalyzed electrophilic substitution by PhSeBr in organoboranes, organosilanes, and organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides

Bhadra, Sukalyan ; Saha, Amit ; Ranu, Brindaban C. (2010) Al2O3-supported Cu-catalyzed electrophilic substitution by PhSeBr in organoboranes, organosilanes, and organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides Journal of Organic Chemistry, 75 (14). pp. 4864-4867. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo100755g

Related URL: http://dx.doi.org/10.1021/jo100755g

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:92839
Deposited On:05 Jun 2012 10:26
Last Modified:05 Jun 2012 10:26

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