Date of Award

2022

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

Abstract

The development of efficient strategies for the synthesis of aryl–halogen bonds is highly desirable due to the prevalence of these moieties in pharmaceuticals, agrochemicals, and organic synthesis. Although there are numerous applications of aryl chlorides in chemistry, an efficient strategy for the preparation of these molecules is underdeveloped. Transition metal-catalyzed decarbonylation provides an efficient and selective approach for aryl–halogen bond formation. There has been significant progress in the development of new decarbonylation strategies, particularly involving aldehydes for the synthesis of new carbon–hydrogen (C–H) bonds or for cross-coupling reactions. However, transition metal-catalyzed decarbonylation methods for carbon–halogen (C–X) bond formation have been less explored. Herein, we report rhodium-catalyzed decarbonylation of aroyl chlorides for the selective formation aryl chlorides. This work opens the door for further investigation and optimization of various decarbonylation methods, including potential exploration into reaction enantioselectivity and expansion to other carbon–halogen (C–X) bonds.

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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