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

被引：58

作者：

Bhadra, Sukalyan ^{[1
]}

Saha, Amit ^{[1
]}

Ranu, Brindaban C. ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 14期

关键词：

SE-SE; EFFICIENT; HALIDES; CLEAVAGE; PHENYL; ACIDS; SELENOESTERS; CHALCOGENIDE; DISELENIDES; DISULFIDES;

D O I：

10.1021/jo100755g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4864 / 4867

页数：4