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

Nick and Al join forces: The nickel‐catalyzed [3+2] cycloaddition between the title compounds gives cyclopentene derivatives in the presence of Me2AlCl. The organoaluminum reagent activates the carbonyl group of the cyclopropyl ketone through coordination of the oxygen atom to the aluminum, and stab...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-12, Vol.50 (50), p.12067-12070
Main Authors: Tamaki, Takashi, Ohashi, Masato, Ogoshi, Sensuke
Format: Article
Language:English
Subjects:
Alkynes
Aluminum
carbocycles
Chlorides
Cycloaddition
Cyclopentene
Derivatives
homogeneous catalysis
Ketones
Nickel
Organic compounds
transition metals
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Summary:Nick and Al join forces: The nickel‐catalyzed [3+2] cycloaddition between the title compounds gives cyclopentene derivatives in the presence of Me2AlCl. 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201106174