4.7 Article

A palladium-catalyzed Heck/[4+1] decarboxylative cyclization cascade to access diverse heteropolycycles by using α-bromoacrylic acids as C1 insertion units

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 20, Pages 5687-5692

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00861g

Keywords

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Funding

  1. National Natural Science Foundation of China [21901071, 21971061]
  2. Natural Science Foundation of Hunan Province [2020JJ5350]
  3. Scientific Research Fund of Hunan Provincial Education Department [18A002, 19B359]
  4. Science and Technology Planning Project of Hunan Province [2018TP1017]

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A novel palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade of alkene-tethered aryl iodides with alpha-bromoacrylic acids is reported, which enables the construction of diverse heteropolycycles in moderate to excellent yields. This reaction involves the formation of three C-C bonds via sequential fused palladacycle formation, C(vinyl)-Br bond activation, and decarboxylation.
A novel palladium-catalyzed Heck/[4 + 1] decarboxylative cyclization cascade of alkene-tethered aryl iodides with alpha-bromoacrylic acids is reported. This strategy employs alpha-bromoacrylic acids as a new C1 synthon to assemble diverse heteropolycycles, such as cyclopenta[de]isoquinolinediones and cyclopenta[de]indolo[2,1-a]isoquinolinones, in moderate to excellent yields. This reaction enables the construction of three C-C bonds via sequential fused palladacycle formation, C(vinyl)-Br bond activation and decarboxylation.

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