4.7 Article

Decarboxylative cyclization of o-chlorobenzoic acids with C,C-palladacycles formed by an aminopalladation/dealkylation strategy to access dibenzo[a,c]carbazoles

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 13, Pages 3414-3419

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00490a

Keywords

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Funding

  1. National Natural Science Foundation of China [21901071, 21971061]
  2. Natural Science Foundation of Hunan Province [2020JJ5350]
  3. Science and Technology Planning Project of Hunan Province [2018TP1017]
  4. Science and Technology Innovation Program of Hunan Province [2021RC4059]

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Herein, a new palladium-catalyzed reaction for the synthesis of dibenzo[a,c]carbazoles has been reported. This method utilizes an intramolecular aminopalladation/dealkylation strategy to form C,C-palladacycles, which can react with o-chlorobenzoic acids to construct one C-N bond and two C-C bonds. The method shows a broad substrate scope and excellent functional group compatibility.
Herein a novel palladium-catalyzed tandem decarboxylative biscyclization of o-alkynylanilines with o-chlorobenzoic acids has been reported, which provides an efficient approach for the assembly of dibenzo[a,c]carbazoles. This protocol employs an intramolecular aminopalladation/dealkylation strategy to form C,C-palladacycles, which allow the construction of one C-N bond and two C-C bonds by reacting with o-chlorobenzoic acids. The method features a broad substrate scope and excellent functional group compatibility.

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