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电化学C(sp)–H氟化反应

Electrochemical C(sp)-H Fluorination.

作者信息

Takahira Yusuke, Chen Miao, Kawamata Yu, Mykhailiuk Pavel, Nakamura Hugh, Peters Byron K, Reisberg Solomon H, Li Chao, Chen Longrui, Hoshikawa Tamaki, Shibuguchi Tomoyuki, Baran Phil S

机构信息

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Enamine Ltd.; Chervonotkatska 78, 02094 Kyiv (Ukraine) and Taras Shevchenko National University of Kyiv; Chemistry Department; Volodymyrska 64, 01601 Kyiv (Ukraine).

出版信息

Synlett. 2019 Jun;30(10):1178-1182. doi: 10.1055/s-0037-1611737. Epub 2019 Mar 1.

Abstract

A simple and robust method for electrochemical alkyl C-H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C-H bonds were converted to their C-F congeners. The scalability of the reaction was also demonstrated with a 100 gram preparation of fluorovaline.

摘要

本文提出了一种简单且稳健的电化学烷基C-H氟化方法。使用一种简单的硝酸盐添加剂、一种广泛可得的氟源(Selectfluor)和碳基电极,多种活化和未活化的C-H键被转化为其C-F同类物。通过制备100克氟缬氨酸也证明了该反应的可扩展性。

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Electrochemical C(sp)-H Fluorination.电化学C(sp)–H氟化反应
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Catalyzed and Promoted Aliphatic Fluorination.催化和促进脂肪族氟化反应
J Org Chem. 2018 Aug 17;83(16):8803-8814. doi: 10.1021/acs.joc.8b00982. Epub 2018 Jul 3.
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Scalable, Electrochemical Oxidation of Unactivated C-H Bonds.可扩展的、电化学氧化未活化的 C-H 键。
J Am Chem Soc. 2017 Jun 7;139(22):7448-7451. doi: 10.1021/jacs.7b03539. Epub 2017 May 23.
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The Uranyl Cation as a Visible-Light Photocatalyst for C(sp(3) )-H Fluorination.铀酰阳离子可见光光催化剂用于 C(sp(3) )-H 氟化。
Angew Chem Int Ed Engl. 2016 Jul 25;55(31):8923-7. doi: 10.1002/anie.201603149. Epub 2016 Jun 20.
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Visible light-promoted metal-free sp(3)-C-H fluorination.可见光促进的无金属sp(3)-C-H氟化反应
Chem Commun (Camb). 2014 Oct 11;50(79):11701-4. doi: 10.1039/c4cc05650g.

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