ダウンロード数: 35
このアイテムのファイル:
ファイル | 記述 | サイズ | フォーマット | |
---|---|---|---|---|
s44160-023-00439-8.pdf | 1.61 MB | Adobe PDF | 見る/開く |
タイトル: | Reductive stereo- and regiocontrolled boryllithiation and borylsodiation of arylacetylenes using flow microreactors |
著者: | Jiang, Yiyuan Kurogi, Takashi Yorimitsu, Hideki |
著者名の別形: | 江, 迤源 黒木, 尭 依光, 英樹 |
キーワード: | Synthetic chemistry methodology Process chemistry Stereochemistry |
発行日: | Feb-2024 |
出版者: | Springer Nature |
誌名: | Nature Synthesis |
巻: | 3 |
号: | 2 |
開始ページ: | 192 |
終了ページ: | 201 |
抄録: | Given their prevalence within valuable organic compounds, constructing multisubstituted alkenes while stereo- and regiochemically controlling the substituents on the alkene stands as a pivotal objective in organic synthesis. Now, the stereo- and regioselective syn-boryllithiation and syn-borylsodiation of arylacetylenes have been achieved by reductive borylmetallation using flow microreactors. This method involves the fast mixing of a solution of an alkyne and stoichiometric alkoxypinacolborane with an alkali metal arenide solution, which efficiently generates highly reactive β-borylalkenyllithium and β-borylalkenylsodium species by suppressing the undesired diboration that inevitably occurs in a batch reactor. Unlike conventional three-component borofunctionalization, the intermediates can be generated in the absence of electrophiles, which has enabled diverse electrophiles to participate in various syn-borofunctionalizations such as borylsilylation, borylhalogenation, borylcarbonylation, borylsulfenylation and borylarylation. Trapping with aldehydes and ketones provides a series of oxaboroles of biological interest. Furthermore, unsymmetric diarylacetylenes undergo highly regioselective borylmetallation, which is applicable to the stereo- and regiocontrolled syntheses of multisubstituted oxaboroles and differently tetrasubstituted alkenes. |
記述: | ミクロ空間内での化学反応で狙った有用物質を製造可能に --電子の注入制御によるグリーンな物質生産--. 京都大学プレスリリース. 2023-11-20. |
著作権等: | © The Author(s) 2023 This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. |
URI: | http://hdl.handle.net/2433/286977 |
DOI(出版社版): | 10.1038/s44160-023-00439-8 |
関連リンク: | https://www.kyoto-u.ac.jp/ja/research-news/2023-11-20-1 |
出現コレクション: | 学術雑誌掲載論文等 |
このアイテムは次のライセンスが設定されています: クリエイティブ・コモンズ・ライセンス