4.7 Article

Visible-light-mediated multi-component carbene transfer reactions of α-diazoesters to construct multisubstituted pyrazoles and 1,3-dicarbonyl derivatives

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 20, Pages 5530-5535

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01082h

Keywords

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Funding

  1. Youth Innovation and Technology Project of High School in Shandong Province [2019KJC021]
  2. Natural Science Foundation of Shandong Province [ZR2021MB065]
  3. CAS Light of West China Program
  4. Qinghai Province Innovation Platform Construction Project [2022-ZJ-Y03]

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A visible-light-mediated strategy for the synthesis of multisubstituted pyrazoles through a three-component carbene transfer reaction of alpha-diazoesters with cyclic ethers and pyrazolones is reported. This transformation can be achieved under mild and additive-free conditions, yielding a wide range of multisubstituted pyrazoles with moderate to good yields and excellent functional group compatibility. Additionally, a series of substituted 1,3-dicarbonyl derivatives can be conveniently obtained via visible-light-promoted three-component reaction of alpha-diazoesters, cyclic ethers, and 1,3-dicarbonyl compounds.
A visible-light-mediated strategy is reported for the efficient synthesis of multisubstituted pyrazoles through a three-component carbene transfer reaction of alpha-diazoesters with cyclic ethers and pyrazolones. The present transformation could be accomplished under mild and additive-free conditions to afford a wide range of multisubstituted pyrazoles with moderate to good yields and excellent functional group compatibility. It is noteworthy that a series of substituted 1,3-dicarbonyl derivatives were also conveniently obtained via visible-light-promoted three-component reaction of alpha-diazoesters, cyclic ethers, and 1,3-dicarbonyl compounds.

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