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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

Synthesis of 1-(Difluoromethyl)alk-1-enes via Palladium-Catalyzed SN2′-Type Substitution Reaction of Difluoromethylated Allylic Phosphates with 1,3-Dicarbonyl Compounds and Imides

http://hdl.handle.net/2237/0002001509
http://hdl.handle.net/2237/0002001509
1a58c864-49d3-4eaf-9358-b047afe6dc33
名前 / ファイル ライセンス アクション
JOC_MS_rev2.pdf JOC_MS_rev2.pdf (1.4 MB)
Item type itemtype_ver1(1)
公開日 2021-10-14
タイトル
タイトル Synthesis of 1-(Difluoromethyl)alk-1-enes via Palladium-Catalyzed SN2′-Type Substitution Reaction of Difluoromethylated Allylic Phosphates with 1,3-Dicarbonyl Compounds and Imides
言語 en
著者 Yamamoto, Yoshihiko

× Yamamoto, Yoshihiko

en Yamamoto, Yoshihiko

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Sakai, Motoji

× Sakai, Motoji

en Sakai, Motoji

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Ishida, Yuki

× Ishida, Yuki

en Ishida, Yuki

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Yasui, Takeshi

× Yasui, Takeshi

en Yasui, Takeshi

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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 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-TH2VRFKBHS8FNFSVMABH].”
内容記述
内容記述 Herein, we report the synthesis of 1-(difluoromethyl)alkenes via a palladium-catalyzed reaction of difluoromethyl-substituted allylic phosphates with 1,3-dicarbonyl compounds using PdCl2(PPh3)2 as a precatalyst. 1,3-Dicarbonyl compounds attacked the γ-carbon with respect to the difluoromethyl group to afford their corresponding SN2′-type substitution products irrespective of the substitution pattern in the allylic phosphates. This regioselectivity has been ascribed to the electronic environment of the unsymmetrical π-allylpalladium intermediate using density functional theory (DFT) calculations. The reaction of difluoromethyl-substituted allylic phosphates with imides was also carried out using a different catalyst system composed of [PdCl(η^3-allyl)]2 and di(diphenylphosphino)butane (dppb).
言語 en
内容記述タイプ Abstract
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
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/10.1021/acs.joc.0c02538
収録物識別子
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 86, 号 1, p. 1053-1064, 発行日 2021-01-01
ファイル公開日
日付 2022-01-01
日付タイプ Available
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