Rapid assembly of tetrahydrodibenzofurans and tetrahydrocarbazoles from benzene and o-iodophenols and o-iodoanilines:: reductive radical arylation of benzene in action

被引：29

作者：

Crich, D ^{[1
]}

Sannigrahi, M ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 17期

基金：

美国国家科学基金会;

关键词：

radicals and radical reactions; dienes; cyclisation; selenium and compounds;

D O I：

10.1016/S0040-4020(02)00288-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of catalytic benzeneselenol, generated in situ from diphenyl diselenide, tributyltin hydride brings about the radical addition of ortho-functionalized aryl iodides to benzene giving aryl cyclohexadienes. These may then be cyclized by means of standard electrophilic reagents. The use of o-methoxycarbamoyliodobenzene leads to a tetrahydrocarbazole, whereas o-iodobenzoic acid provides a tetrahydrodibenzopyranone. o-Iodophenois lead, overall, to tetrahydrodibenzofurans. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3319 / 3322

页数：4

共 16 条

[1] Facile allylative dearomatization catalyzed by palladium [J].