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Mechanism of 2,6-Dichloro-4,4 '-bipyridine-Catalyzed Diboration of Pyrazines Involving a Bipyridine-Stabilized Boryl Radical

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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
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
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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