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  1. D400 創薬科学研究科
  2. D400a 雑誌掲載論文
  3. 学術雑誌

Theoretical Study of the Copper-Catalyzed Hydroarylation of (Trifluoromethyl)alkyne with Phenylboronic Acid

http://hdl.handle.net/2237/00029250
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
JOC_MS_Rev2.pdf JOC_MS_Rev2 (2.7 MB)
Item type 学術雑誌論文 / Journal Article(1)
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
言語 en
著者 Yamamoto, Yoshihiko

× Yamamoto, Yoshihiko

WEKO 88613

en Yamamoto, Yoshihiko

Search repository
アクセス権
アクセス権 open access
アクセス権URI http://purl.org/coar/access_right/c_abf2
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.
言語 en
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
言語 ja
内容記述タイプ Other
出版者
言語 en
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
出版タイプ
出版タイプ AM
出版タイプResource http://purl.org/coar/version/c_ab4af688f83e57aa
DOI
関連タイプ isVersionOf
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 PISSN
収録物識別子 0022-3263
書誌情報 en : The Journal of Organic Chemistry

巻 83, 号 20, p. 12775-12783, 発行日 2018-10-19
著者版フラグ
値 author
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