[3+2] Cycloaddition Reaction of Cyclopropyl Ketones with Alkynes Catalyzed by Nickel/Dimethylaluminum Chloride

被引：74
|
作者：
Tamaki, Takashi [1 ]
Ohashi, Masato [1 ,2 ]
Ogoshi, Sensuke [1 ]
机构：
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Ctr Atom & Mol Technol, Suita, Osaka 5650871, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 50期
基金：
日本学术振兴会;
关键词：
carbocycles; cycloaddition; homogeneous catalysis; nickel; transition metals; ETHYL CYCLOPROPYLIDENEACETATE; OXIDATIVE CYCLIZATION; KEY INTERMEDIATE; BOND ACTIVATION; NICKEL; METHYLENECYCLOPROPANES; COCYCLIZATION; ENONES; ARYL; ALK-5-YNYLIDENECYCLOPROPANES;
D O I：
10.1002/anie.201106174
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Nick and Al join forces: The nickel-catalyzed [3+2] cycloaddition between the title compounds gives cyclopentene derivatives in the presence of Me 2AlCl. The organoaluminum reagent activates the carbonyl group of the cyclopropyl ketone through coordination of the oxygen atom to the aluminum, and stabilizes the reaction intermediate by the coordination of the chloride to nickel. cod=1,5-cyclooctadiene, THF=tetrahydrofuran. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：12067 / 12070
页数：4
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