4.8 Article

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Journal

ORGANIC LETTERS
Volume 22, Issue 14, Pages 5582-5588

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01937

Keywords

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Funding

  1. NSFC [21801029]
  2. Graduate Scientific Research and Innovation Foundation of Chongqing [CYS18046]
  3. Sichuan Key Laboratory of Medical Imaging (North Sichuan Medical College) [SKLMI201901]
  4. Nanchong City [19SXHZ0441]
  5. North Sichuan Medical College [19SXHZ0441]
  6. Chongqing Postdoctoral Science Foundation [cstc2019jcyj-bshx0057]
  7. Fundamental Research Funds for the Central Universities [2020CDJQY-A043]
  8. Natural Science Foundation of Chongqing [cstc2019jcyj-msxmX0048]

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Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multi-substituted arenes. Preliminary mechanistic studies suggest that a Fe-II/Fe-III catalytic cycle via a radical pathway might be involved in the reaction.

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