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[3+2] Cycloaddition Reaction of Cyclopropyl Ketones with Alkynes Catalyzed by Nickel/Dimethylaluminum Chloride
Author(s) -
Tamaki Takashi,
Ohashi Masato,
Ogoshi Sensuke
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106174
Subject(s) - cycloaddition , chemistry , nickel , cyclopentene , catalysis , chloride , reagent , ketone , medicinal chemistry , tetrahydrofuran , organic chemistry , solvent
Nick and Al join forces : The nickel‐catalyzed [3+2] cycloaddition between the title compounds gives cyclopentene derivatives in the presence of Me 2 AlCl. 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.