4.6 Article

Iron-catalyzed decarbonylative borylation enables the one-pot diversification of (Hetero) Aryl and alkyl carboxylic acids

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CELL REPORTS PHYSICAL SCIENCE
卷 3, 期 8, 页码 -

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ELSEVIER
DOI: 10.1016/j.xcrp.2022.100995

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资金

  1. Fundamental Research Funds for the Central Universities [2021CDJQY-020]
  2. Natural Science Foundation of Sichuan [2021YJ0413]
  3. Sichuan Key Laboratory of Medical Imaging (North Sichuan Medical College) [SKLMI201901]
  4. Strategic Cooperation of Science and Technology between Nanchong City and North Sichuan Medical College [19SXHZ0441, 19SXHZ0227]
  5. Chongqing Postdoctoral Science Foundation [cstc2019jcyj-bshx0057]
  6. China Postdoctoral Science Foundation [2020M673121]
  7. Analytical and Testing Center of Chongqing University

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In this study, iron-catalyzed decarbonylation of aryl and alkyl carboxylic acids has been developed, providing the corresponding borylated products with good efficiency. This protocol features excellent functional group compatibility and mild conditions, offering new opportunities for applications in medicinal chemistry and organic synthesis.
Carboxylic acids are cheap, abundant, and environmentally friendly and are widely employed as partners in cross-coupling reactions. Transition-metal-catalyzed carboxylic acid transformations are typically achieved at extreme temperatures (usually >150 degrees C), significantly limiting their practicality. Here, iron-catalyzed decarbonylation of aryl and alkyl carboxylic acids has been developed, providing the corresponding borylated products with good efficiency. This protocol features excellent functional group compatibility, mild conditions, and the late-stage borylation of bio-relevant carboxylic acids, thus offering excellent opportunities for applications in medicinal chemistry and organic synthesis. Preliminary mechanistic studies suggest that the iron(I)-boryl species may be the crucial intermediate and that a decarbonylative process is involved in this catalytic transformation.

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