Rhodium-Catalyzed Acylation with Quinolinyl Ketones: Carbon−Carbon Single Bond Activation as the Turnover-Limiting Step of Catalysis

The rhodium-catalyzed intramolecular carboacylation of quinolinyl ketones serves as an ideal subject for the mechanistic study of carbon−carbon bond activation. Combined kinetic and NMR studies of this reaction allowed the identification of the catalytic resting state and determination of the rate l...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-02, Vol.133 (7), p.2031-2033
Main Authors: Rathbun, Colin M, Johnson, Jeffrey B
Format: Article
Language:English
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Summary:The rhodium-catalyzed intramolecular carboacylation of quinolinyl ketones serves as an ideal subject for the mechanistic study of carbon−carbon bond activation. Combined kinetic and NMR studies of this reaction allowed the identification of the catalytic resting state and determination of the rate law, 12C/13C kinetic isotope effects, and activation parameters. These results have identified the activation of a ketone−arene carbon−carbon single bond as the turnover-limiting step of catalysis and provided quantitative detail into this process.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja109686v