Development of an electrochemical C(sp<sup>3</sup>)-H fluorination reaction

DOI
  • Hoshikawa Tamaki
    Hatfield Research Laboratories, Discovery, Medicine Creation, Neurology Business Group, Eisai Co., Ltd.
  • Shibuguchi Tomoyuki
    Talent Management Department, Eisai Co., Ltd., Japan Pharmaceutical Manufacturers Association
  • Kurokawa Toshiki
    Portfolio Department, Discovery, Medicine Creation, Neurology Business Group, Eisai Co., Ltd.
  • Yoshimura Hikaru
    Neurology Tsukuba Research Laboratories, Discovery, Medicine Creation, Neurology Business Group, Eisai Co., Ltd.
  • Baran Phil S.
    Department of Chemistry, The Scripps Research Institute (TSRI)

Bibliographic Information

Other Title
  • 電解化学に基づく不活性C(sp<sup>3</sup>)-H結合のフッ素化反応の開発

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Description

<p>A novel method for electrochemical C(sp3)-H fluorination has been developed under an academia-industry collaborative research. Using Selectfluor and a nitrate salt, a wide range of aliphatic C-H bonds can be converted to C-F bonds in a single step without the requirement of existing functional groups. Here we describe the detail of our collaborative research, including protocol optimization, substrate scope and limitations, and its application to Eisai in-house compounds, especially to tropane compounds. The impact of fluorination on drug-likeness properties was also assessed, and significant improvements on P-gp liability and hERG/Nav 1.5 inhibitory were observed.</p>

Journal

  • MEDCHEM NEWS

    MEDCHEM NEWS 30 (3), 145-149, 2020-08-01

    The Pharmaceutical Society of Japan

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