Synthesis of 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene from the Sonogashira reactions of 2-aryl-1,1-dibromoethene

被引：23

作者：

Lee, HB ^{[1
]}

Huh, DH ^{[1
]}

Oh, JS ^{[1
]}

Min, GH ^{[1
]}

Kim, BH ^{[1
]}

Lee, DH ^{[1
]}

Hwang, JK ^{[1
]}

Kim, YG ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Engn, Sch Chem Engn, Seoul 151744, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 39期

关键词：

coupling reactions; diyne; enyne; palladium and compounds;

D O I：

10.1016/S0040-4020(01)00829-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene were produced from the Sonogasbira reactions of 2-aryl-1,1-dibromoethene with 1-alkyne. The ratio of the products varied according to the reaction conditions. The coupling reactions in benzene afforded the 2-aryl-1,1-dialkynylethene as a major product and no 1-aryl-1,3-diyne was isolated. The 1-aryl-1,3-diyne could be obtained in DMF in acceptable yields. When amines were used as a reaction solvent, the coupling reaction gave the 2-aryl-1, 1-dialkynylethene (20%) and the conjugated enyne (68%) in diisopropylamine, whereas only the 1-aryl-1,3-diyne was isolated in piperidine in 56% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8283 / 8290

页数：8

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