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Theoretical Study of the Copper-Catalyzed Hydroarylation of (Trifluoromethyl)alkyne with Phenylboronic Acid
http://hdl.handle.net/2237/00029250
15d899e4-7d7a-4336-bc40-b6e74727e424
名前 / ファイル | ライセンス | アクション | |
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2019-02-06 | |||||
タイトル | ||||||
タイトル | Theoretical Study of the Copper-Catalyzed Hydroarylation of (Trifluoromethyl)alkyne with Phenylboronic Acid | |||||
著者 |
Yamamoto, Yoshihiko
× Yamamoto, Yoshihiko |
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権利 | ||||||
権利情報 | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in [The Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-G3FHkxUG9drwD4N3feiH].” | |||||
抄録 | ||||||
内容記述 | The copper-catalyzed hydroarylation of 1,1,1-trifluoro-2-butyne with phenylboronic acid was investigated by performing density functional theory calculations, and a plausible mechanism was proposed. The initial transmetalation step was first examined to compare the feasibility of the catalytically active copper species. Subsequently, the carbocupration of 1,1,1-trifluoro-2-butyne by the phenylcopper species was examined in terms of regioselectivity. The impacts of the alkyne terminal group and the para-substituents of phenylboronic acids on the carbocupration were also examined. Moreover, to shed light on the role of the electron-withdrawing groups on the alkyne substrates, the activation barrier for the carbocupration of 1,1,1-trifluoro-2-butyne was compared to those for several alkyne substrates bearing ester, ketone, cyano, and pentafluorophenyl groups, as well as 2-butyne, which has no electron-withdrawing group. The final protodecupration step involving methanol, acetic acid, or phenylboronic acid was examined to determine possible proton donors. | |||||
内容記述タイプ | Abstract | |||||
内容記述 | ||||||
内容記述 | ファイル公開:2019-10-19 | |||||
内容記述タイプ | Other | |||||
出版者 | ||||||
出版者 | ACS Publications | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプresource | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | journal article | |||||
DOI | ||||||
関連識別子 | ||||||
識別子タイプ | DOI | |||||
関連識別子 | https://doi.org/10.1021/acs.joc.8b02215 | |||||
ISSN(print) | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0022-3263 | |||||
書誌情報 |
The Journal of Organic Chemistry 巻 83, 号 20, p. 12775-12783, 発行日 2018-10-19 |
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著者版フラグ | ||||||
値 | author |