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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

1,2‐Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull‐Push Reactivity of Tris(pentafluorophenyl)borane

http://hdl.handle.net/2237/0002001675
http://hdl.handle.net/2237/0002001675
ac228391-72e8-44ae-8d23-d5de79ac6f59
名前 / ファイル ライセンス アクション
CEJ2021.pdf CEJ2021.pdf (1.5 MB)
Item type itemtype_ver1(1)
公開日 2021-12-07
タイトル
タイトル 1,2‐Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull‐Push Reactivity of Tris(pentafluorophenyl)borane
言語 en
著者 Shibuya, Masatoshi

× Shibuya, Masatoshi

en Shibuya, Masatoshi

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Matsuda, Miki

× Matsuda, Miki

en Matsuda, Miki

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Yamamoto, Yoshihiko

× Yamamoto, Yoshihiko

en Yamamoto, Yoshihiko

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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
言語 en
権利情報 "This is the peer reviewed version of the following article: [M. Shibuya, M. Matsuda, Y. Yamamoto, Chem. Eur. J. 2021, 27, 8822.], which has been published in final form at [https://doi.org/10.1002/chem.202101090]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited."
内容記述
内容記述 We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C−C bond formation with C−H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C−C bond with C−O bond scission at the silyloxy-substituted carbon.
言語 en
内容記述タイプ Abstract
出版者
言語 en
出版者 Wiley
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
関連情報
関連タイプ isVersionOf
識別子タイプ DOI
関連識別子 https://doi.org/10.1002/chem.202101090
収録物識別子
収録物識別子タイプ PISSN
収録物識別子 0947-6539
書誌情報 en : Chemistry – A European Journal

巻 27, 号 34, p. 8822-8831, 発行日 2021-06-16
ファイル公開日
日付 2022-06-16
日付タイプ Available
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