Title

Rhodium-Catalyzed Carboacylation with Quinolinyl Ketones: Evidence for Rate-Limiting C-C Bond Activation

Faculty Mentor(s)

Dr. Jeffrey Johnson, Hope College

Document Type

Poster

Publication Date

4-15-2011

Comments

This work is supported by the Research Corporation.

Abstract

Carbon-carbon single bond activation reactions promise to revolutionize organic synthesis by opening the doors to new, more efficient synthetic methods. 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.

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