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External Flash Generation of Carbenoids Enables Monodeuteration of Dihalomethanes
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- Kazuhiro Okamoto
- Department of Chemistry, Graduate School of Science Hokkaido University Sapporo 060-0810 Japan
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- Ryosuke Higuma
- Department of Synthetic and Biological Chemistry Graduate School of Engineering Kyoto University Nishikyo-ku Kyoto 615-8510 Japan
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- Kensuke Muta
- Fundamental Chemical Research Center Central Glass Co., Ltd. 17-5, Nakadai 2-chome, Kawagoe City Saitama 350-1159 Japan
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- Keita Fukumoto
- Department of Synthetic and Biological Chemistry Graduate School of Engineering Kyoto University Nishikyo-ku Kyoto 615-8510 Japan
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- Yuta Tsuchihashi
- Taiyo Nippon Sanso Corp. 10 Okubo, Tsukuba-shi Ibaraki 300-2611 Japan
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- Yosuke Ashikari
- Department of Chemistry, Graduate School of Science Hokkaido University Sapporo 060-0810 Japan
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- Aiichiro Nagaki
- Department of Chemistry, Graduate School of Science Hokkaido University Sapporo 060-0810 Japan
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Description
<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>
Journal
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- Chemistry – A European Journal
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Chemistry – A European Journal 29 (47), e202301738-, 2023-07-18
Wiley