Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis

被引：94

作者：

Kinoshita, A ^{[1
]}

Sakakibara, N ^{[1
]}

Mori, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 27期

关键词：

enyne metathesis; diene; ruthenium; metathesis; alkyne metathesis; ethylene;

D O I：

10.1016/S0040-4020(99)00297-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel 1,3-diene synthetic method from alkyne and ethylene was developed using ruthenium-catalyzed enyne metathesis. The reaction procedure is very simple: A CH2Cl2 solution of alkyne was stirred at room temperature under ethylene gas (1 atm.) in the presence of a catalytic amount of ruthenium benzylidene complex. The yield was good and the conversion yield was high. Dienes having functional groups such as a keto-carbonyl group, silyloxy group, ester, and ketal were synthesized from the corresponding alkynes and ethylene. In this reaction, the alkyne having a hetero atom at the propargylic position gave a good result and ether oxygen or amine nitrogen that coordinate strongly to the ruthenium catalyst prevents the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8155 / 8167

页数：13

共 56 条

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