An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis

被引：81

作者：

Tonogaki, K ^{[1
]}

Mori, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(02)00215-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of 1,3-diene from alkyne and ethylene (I atm) was improved using ruthenium carbene complex lb having heterocyclic carbene as a ligand. In this reaction, the heteroatom at the propargylic position was not required, although the reaction of alkyne with the first-generation ruthenium carbene complex la was affected by the substituent at the propargylic position. Various 1,3-dienes could be synthesized from alkynes and ethylene. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：2235 / 2238

页数：4

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[31] SELECTIVITY OF OLIGOMERIZATION OF 1,3-DIENE BY USING THE COMPLEX CATALYSTS [J].

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