External Flash Generation of Carbenoids Enables Monodeuteration of Dihalomethanes

  • Kazuhiro Okamoto
    Department of Chemistry, Graduate School of Science Hokkaido University Sapporo 060-0810 Japan
  • Ryosuke Higuma
    Department of Synthetic and Biological Chemistry Graduate School of Engineering Kyoto University Nishikyo-ku Kyoto 615-8510 Japan
  • Kensuke Muta
    Fundamental Chemical Research Center Central Glass Co., Ltd. 17-5, Nakadai 2-chome, Kawagoe City Saitama 350-1159 Japan
  • Keita Fukumoto
    Department of Synthetic and Biological Chemistry Graduate School of Engineering Kyoto University Nishikyo-ku Kyoto 615-8510 Japan
  • Yuta Tsuchihashi
    Taiyo Nippon Sanso Corp. 10 Okubo, Tsukuba-shi Ibaraki 300-2611 Japan
  • Yosuke Ashikari
    Department of Chemistry, Graduate School of Science Hokkaido University Sapporo 060-0810 Japan
  • Aiichiro Nagaki
    Department of Chemistry, Graduate School of Science Hokkaido University Sapporo 060-0810 Japan

説明

<jats:title>Abstract</jats:title><jats:p>In this study, incorporation of one deuterium atom was achieved by H−D exchange of one of the two identical methylene protons in various dihalomethanes (halogen=Cl, Br, and I) through a rapid‐mixing microflow reaction of lithium diisopropylamide as a strong base and deuterated methanol as a deuteration reagent. Generation of highly unstable carbenoid intermediate and suppression of its decomposition were successfully controlled under high flow‐rate conditions. Monofunctionalization of diiodomethane afforded various building blocks composed of boryl, stannyl, and silyl groups. The monodeuterated diiodomethane, which served as a deuterated C1 source, was subsequently subjected to diverted functionalization methods to afford various products including biologically important molecules bearing isotope labelling at specific positions and homologation products with monodeuteration.</jats:p>

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詳細情報 詳細情報について

  • CRID
    1360862099306097280
  • DOI
    10.1002/chem.202301738
  • ISSN
    15213765
    09476539
  • データソース種別
    • Crossref

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