General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium

被引：37

作者：

Bieber, LW ^{[1
]}

de Sá, ACPF ^{[1
]}

Menezes, PH ^{[1
]}

Gonçalves, SMC ^{[1
]}

机构：

[1] Univ Fed Pernambuco, Dept Quim, BR-50670901 Recife, PE, Brazil

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(01)00820-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, alpha -bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a S(H)2 mechanism via alkyl radicals. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4597 / 4599

页数：3

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