Advances in Cobalt Catalysis for Carbene Insertion

Author

• Keyang Wu, Utah State UniversityFollow

Date of Award:

8-2026

Document Type:

Dissertation

Degree Name:

Doctor of Philosophy (PhD)

Department:

Chemistry and Biochemistry

Committee Chair(s)

Gang Li

Committee

Gang Li

Committee

Cheng-Wei Tom Chang

Committee

Yi Rao

Committee

Yunfan Qiu

Committee

Dian Wang

Abstract

Carbenes are versatile intermediates capable of undergoing diverse transformations, particularly insertion reactions. While carbene insertion chemistry has been extensively developed with noble metal catalysts and primarily earth abundant metals such as copper and iron, analogous reactions catalyzed by cobalt remain underexplored. This work establishes a new cobalt catalyzed platform for carbene insertion into X–H bonds using cobaloxime complexes. These cobalt-based catalysts provide an efficient and selective approach to X–H insertion chemistry, offering broad potential for synthetic applications.

The first part of this research focuses on cobaloxime-catalyzed carbene insertion into N–H bonds, providing a facile route to synthesize α-amino esters. This transformation provides an efficient strategy for C–N bond formation, a fundamental process in the synthesis of pharmaceuticals, agrochemicals, and natural products. The second part extends this strategy to analogous insertion reactions catalyzed by cobaloximes, affording a range of valuable products, including α-amino esters as well as α-oxygenated esters, which serve as versatile building blocks in pharmaceutical and materials science. Finally, this research explores cobaloxime-catalyzed carbene insertion into B–H bonds to access novel α-boryl esters. These organoboron compounds are synthetically important due to their ability to undergo diverse downstream transformations.

In summary, this work advances cobalt catalyzed carbene insertion into N–H, O–H, and B–H bonds, demonstrating that cobaloxime complexes are efficient and versatile catalysts. These results broaden the scope of carbene insertion chemistry and offer a sustainable, cost-effective approach for preparing pharmaceutically and industrially relevant compounds.

Recommended Citation

Wu, Keyang, "Advances in Cobalt Catalysis for Carbene Insertion" (2026). All Graduate Theses and Dissertations, Fall 2023 to Present. 815.
https://digitalcommons.usu.edu/etd2023/815