Faculty Sponsor
Dr. Upendra Sharma
Final Abstract for URS Program
Visible-Light-Promoted Nickel-Catalyzed Suzuki Coupling of Alkene-Derived Alkyl-BBN with Aryl Halides
Naomi Collis,† Rajesh Kumar†, Upendra K. Sharma*†
†Department of Chemistry and Biochemistry, University of Missouri-St. Louis, 1 University Boulevard, St. Louis, MO 63121, USA.
E-mail: [email protected]
Abstract:
Traditional cross‑coupling reactions, such as Suzuki-Miyaura,1 Negishi,2 and Stille couplings,3 often require harsh conditions (e.g., high temperatures), pre‑functionalized starting materials, and relatively toxic reagents, which limit substrate scope and generate significant waste. To overcome these limitations, light‑driven nickel catalysis has emerged as a powerful alternative that operates under mild, room‑temperature conditions.4 The present study highlights the utility of light‑promoted, nickel‑catalyzed Suzuki coupling of alkene‑derived alkyl‑BBN intermediates with aryl halides. In this approach, the alkenes are first converted in situ into the corresponding alkyl‑9‑BBN species via hydroboration, which subsequently undergo nickel‑catalyzed cross‑coupling under visible‑light irradiation at room temperature. This strategy enables efficient construction of C(sp3)-C(sp2) bonds from readily available alkenes and aryl halides. The in‑situ generation of alkyl‑BBN intermediates eliminates the need for pre‑synthesized organoboron reagents, thereby improving operational simplicity and step economy. Overall, this sequential hydroboration/photochemical nickel‑catalyzed Suzuki coupling provides a practical and versatile platform for C-C bond formation.
Keywords: Alkene, Cross-coupling, Ni-catalysis, Photocatalysis, Suzuki Coupling
References:
1) Martin, R.; Buchwald, S.-L. Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands. Acc. Chem. Res. 2008, 41, 1461-1473.
2) Zhou, J.; C.-F. Gregory. Palladium-Catalyzed Negishi Cross-Coupling Reactions of Unactivated Alkyl Iodides, Bromides, Chlorides, and Tosylates. J. Am. Chem. Soc. 2003, 125, 12527-12530.
3) Cordovilla, C.; Bartolomé, C.; Martínez-Ilarduya, J. M.; Espinet, P. The Stille Reaction, 38 Years Later. ACS Catal. 2015, 5, 3040-3053.
4) a) Cheung, K. P. S.; Sarkar, S.; Gevorgyan, V. Visible light-induced transition metal catalysis. Chem. Rev. 2022, 122, 1543-1625; b) Li, J.; Zhang, D.; Hu, Z. Ligand-enabled “two-in-one” metallaphotocatalytic cross couplings. ACS Catal. 2025, 15, 1635-1654.
Presentation Type
Visual Presentation
Document Type
Article