4.7 Article

Aziridine used as a vinylidene unit in palladium-catalyzed [2+2+1] domino annulation

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 13, Pages 3413-3420

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00458a

Keywords

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Funding

  1. National Natural Science Foundation of China [21901265]
  2. Guizhou Provincial Natural Science Foundation [QKHJC-2020-1Z072]
  3. Outstanding Youth Talent Support Programs from Zunyi Medical University [18ZY-002]
  4. Science and Technology Department of Zunyi [ZSKRPT-2020-5]
  5. Fifth Batch of Talent Base in Guizhou Province [S-030-1]

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A novel palladium-catalyzed three-component reaction has been developed, which utilizes three different types of compounds to produce a range of new compounds in moderate to good yields. Significantly, aziridine was used as a vinylidene unit for the first time in the products.
A novel palladium-catalyzed three-component reaction of 3-iodochromones with bridged olefins and aziridine is described, which employs a [2 + 2 + 1] domino annulation strategy to produce chromone fused methylenecyclopentanes in moderate to good yields via a Heck coupling/C(sp(2))-H activation/imine-enamine tautomerization/retro-aza-Michael addition sequence. Significantly, aziridine was used as a vinylidene unit by cleavage of two C-N bonds and was successfully introduced into the products for the first time.

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