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

Document Type

Article

Publication Date

2-23-2011

Publication Source

Journal of the American Chemical Society

Volume Number

133

Issue Number

7

First Page

2031

Last Page

2033

Publisher

American Chemical Society

ISSN

0002-7863

Abstract

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, C-12/C-13 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.

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