Regioselective cobalt-catalyzed Diels-Alder reaction towards 1,3-disubstituted and 1,2,3-trisubstituted benzene derivatives

被引：53

作者：

Hilt, Gerhard ^{[1
]}

Danz, Michael ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

来源：

SYNTHESIS-STUTTGART | 2008年 / 14期

关键词：

alkyne; cobalt; Diels-Alder; diene; Wittig olefination;

D O I：

10.1055/s-2008-1078450

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward reaction sequence consisting of the Wittig olefination of aldehydes utilizing allyltriphenylphosphonium bromide for the generation of 1-substituted 1,3-dienes, cobalt-catalyzed neutral Diels-Alder reaction with terminal and internal alkynes, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation of the dihydroaromatic intermediates leads to regiochemically enriched biphenyl, terphenyl, and silyl-functionalized benzene derivatives in good to excellent yields. Starting from a 1,3-diyne and a 1,3-diene, the reaction sequence consisting of cobalt-catalyzed Diets-Alder reaction, DDQ oxidation, and cobalt-catalyzed cyclotrimerization with acetylene gave an axially chiral biphenyl-terphenyl product.

引用

页码：2257 / 2263

页数：7

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