Journal
ACS OMEGA
Volume 5, Issue 37, Pages 24018-24032Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.0c03415
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Funding
- National Science Foundation [CHE-1609880, CHE-1566059]
- Welch Foundation [AT1740]
- Eugene McDermott Foundation
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Nickel catalysts represent a low cost and environmentally friendly alternative to palladium-based catalytic systems for Suzuki-Miyaura cross-coupling (SMC) reactions. However, nickel catalysts have suffered from poor air, moisture, and thermal stabilities, especially at high catalyst loading, requiring controlled reaction conditions. In this report, we examine a family of mono- and dinuclear Ni(II) and Pd(II) complexes with a diverse and versatile alpha-diimine ligand environment for SMC reactions. To evaluate the ligand steric effects, including the bite angle in the reaction outcomes, the structural variation of the complexes was achieved by incorporating iminopyridine- and acenaphthene-based ligands. Moreover, the impact of substrate bulkiness was investigated by reacting various aryl bromides with phenylboronic acid, 2-naphthylboronic acid, and 9-phenanthracenylboronic acid. Yields were the best with the dinuclear complex, being nearly quantitative (93-99%), followed by the mononuclear complexes, giving yields of 78- 98%. Consequently, alpha-diimine-based ligands have the potential to deliver Ni-based systems as sustainable catalysts in SMC.
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