Nickel Catalyzed Suzuki-Miyaura Cross-Coupling: Reaction Screening and Catalyst Comparison via High-Throughput Experimentation
| dc.contributor.author | Peel-Smith, Daelin | |
| dc.date.accessioned | 2024-03-17T03:15:16Z | |
| dc.date.available | 2024-03-17T03:15:16Z | |
| dc.date.issued | 2024 | |
| dc.description.abstract | Further advances in nickel catalyzed Suzuki-Miyaura cross coupling (SMC) are necessary to enable its broader utilization in academic laboratories and pharmaceutical synthesis. Current challenges include the need for Ni(0) precatalysts with improved stability and reactivity profiles, as well as the dearth of information available regarding substrate specific ligand compatibility. Here, high-throughput experimentation (HTE) techniques were used to compare commercially available and novel Ni(0) precatalysts in SMC reactions while simultaneously investigating trends in ligand pairing for challenging heterocyclic substrates. Once optimized reaction conditions were determined, this enabled the screening of three organohalide coupling partners with progressively increasing nitrogen content against a selection of six diverse ligands. These screens demonstrated the performance of Ni(0) precatalysts developed recently in our group, and highlighted specific ligand viability for heteroatom rich Ni catalyzed SMC reactions. Furthermore, motivated by relevance to the synthesis of the antimalarial drug candidate Ganaplacide, the cross coupling of an imidazole substrate is demonstrated here with a maximum yield of 32%. This work encourages further investigation of the versatile novel Ni(0) precatalysts assessed herein, and enables further optimization of imidazole functionalization with the longer term goal of synthesizing Ganaplacide utilizing Ni catalyzed cross coupling. | |
| dc.description.reviewstatus | Reviewed | |
| dc.description.scholarlevel | Undergraduate | |
| dc.description.sponsorship | Jamie Cassels Undergraduate Research Awards (JCURA) | |
| dc.identifier.uri | https://hdl.handle.net/1828/16185 | |
| dc.language.iso | en | |
| dc.publisher | University of Victoria | |
| dc.subject | High-throughput experimentation | |
| dc.subject | catalysis | |
| dc.subject | science | |
| dc.subject | chemistry | |
| dc.title | Nickel Catalyzed Suzuki-Miyaura Cross-Coupling: Reaction Screening and Catalyst Comparison via High-Throughput Experimentation | |
| dc.type | Poster |