|
Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Science / Faculty of Science >
Peer-reviewed Journal Articles, etc >
Highly chemoselective ligands for Suzuki-Miyaura cross-coupling reaction based on virtual ligand-assisted screening
| Title: | Highly chemoselective ligands for Suzuki-Miyaura cross-coupling reaction based on virtual ligand-assisted screening |
| Authors: | Matsuoka, Wataru Browse this author | | Harabuchi, Yu Browse this author | | Nagata, Yuuya Browse this author | | Maeda, Satoshi Browse this author |
| Issue Date: | 24-May-2023 |
| Publisher: | Royal Society of Chemistry |
| Journal Title: | Organic & biomolecular chemistry |
| Publisher DOI: | 10.1039/d3ob00398a |
| Abstract: | Ligand screening is a crucial step in the development of transition metal catalysis, as it involves identifying the optimal ligand for a particular reaction from a large pool of candidate molecules. Conventionally, this process is performed through an experimental trial-and-error, which can be time-consuming and resource-intensive in many cases. One of the ideal strategies for streamlining this process is a transition state theory (TST)-based approach, which aims to design optimal catalysts that results in the best energy profile for the desired reaction. However, the implementation of TST-based ligand screening remains challenging mainly due to the large number of potential ligands that need to be individually evaluated through quantum chemical calculations. In this study, we experimentally demonstrated a practical TST-based ligand screening in accordance with our virtual ligand-assisted (VLA) screening strategy. As a case study, the electronic anc steric features of phosphine ligands that maximize chemoselectivity in the Suzuki-Miyaura cross-coupling (SMC) reaction of p-chlorophenyl triflate were determined through quantum chemical calculations using virtual ligands, and several phosphine ligands were suggested to exhibit high chemoselectivity. Based on this suggestion, we successfully found that tri(1-adamantyl)phosphine and tri(neopentyl)phosphine show high to excellent selectivity for the C-Cl bond activation. This case study suggests that the VLA screening strategy could be a useful tool for ligand screening. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/89325 |
| Appears in Collections: | 理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
|
Submitter: 松岡 和
|
