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Hokkaido University Collection of Scholarly and Academic Papers >
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Mechanism of 2,6-Dichloro-4,4 '-bipyridine-Catalyzed Diboration of Pyrazines Involving a Bipyridine-Stabilized Boryl Radical
| Title: | Mechanism of 2,6-Dichloro-4,4 '-bipyridine-Catalyzed Diboration of Pyrazines Involving a Bipyridine-Stabilized Boryl Radical |
| Authors: | Ohmura, Toshimichi Browse this author | | Morimasa, Yohei Browse this author | | Ichino, Tomoya Browse this author | | Miyake, Yusuke Browse this author | | Murata, Yasujiro Browse this author | | Suginome, Michinori Browse this author | | Tajima, Kunihiko Browse this author | | Taketsugu, Tetsuya Browse this author | | Maeda, Satoshi Browse this author →KAKEN DB |
| Keywords: | Organocatalyst | | Boryl radical | | Diboration |
| Issue Date: | Jul-2021 |
| Publisher: | 日本化学会（Chemical Society of Japan） |
| Journal Title: | Bulletin of the chemical society of Japan |
| Volume: | 94 |
| Issue: | 7 |
| Start Page: | 1894 |
| End Page: | 1902 |
| Publisher DOI: | 10.1246/bcsj.20210145 |
| Abstract: | The mechanism of 4,4'-bipyridine-catalyzed diboration of pyrazines was studied by experimental observation of the inter-mediates and by theoretical calculations. Intermediary radical species were detected by ESR measurement of the reactions of 2,6-dichloro-4,4'-bipyridines with bis(pinacolato)diboron and identified by simulation. Based on these observations, radical processes involving 4,4'-bipyridine-stabilized boryl radicals were evaluated by DFT calculations combined with singlecomponent artificial force induced reaction (SC-AFIR). The results of calculations indicate that a radical transfer process from 4,4'-bipyridine-stabilized boryl radical to pyrazine is a major pathway in the catalytic reaction. The origin of the high catalytic efficiency of 2,6-dichloro-4,4'-bipyridine is ascribed to the effect of the chlorine atom on the stability of the corresponding N,N'-diboryl-4,4'-bipyridinylidene. |
| Type: | article |
| URI: | http://hdl.handle.net/2115/82921 |
| 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)
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