Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones

Wen, Kangmei; Wu, Yinrong; Chen, Jiewen; Shi, Jie; Zheng, Minjie; Yao, Xingang; Tang, Xiaodong

doi:10.1021/acsomega.1c06443

Cited by 6 publications

(14 citation statements)

References 54 publications

(22 reference statements)

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“…Furthermore, the reaction of chromone 6 with 3-indoleacetic acid 2a cannot provide the product 3aa , suggesting that 6 was not the reactive intermediate. Based on the above observation and previous literature, ,, a possible pathway was proposed. First, the reaction of 1a with copper salt formed copper carboxylate intermediate A .…”

Section: Results and Discussionmentioning

confidence: 90%

“…Based on the above observation and previous literature, ,, a possible pathway was proposed. First, the reaction of 1a with copper salt formed copper carboxylate intermediate A . Elimination of CO 2 from intermediate A afforded organocopper intermediate B .…”

Section: Results and Discussionmentioning

confidence: 90%

“…First, the reaction of 1a with copper salt formed copper carboxylate intermediate A . Elimination of CO 2 from intermediate A afforded organocopper intermediate B . Subsequently, intermediate B reacted with 1a and followed by deprotonation provided intermediate D .…”

Section: Results and Discussionmentioning

confidence: 99%

“…Subsequently, intermediate B reacted with 1a and followed by deprotonation provided intermediate D . Reductive elimination of intermediate D generated the intermediate E . Intramolecular cyclization of intermediate E gave intermediate F .…”

Section: Results and Discussionmentioning

confidence: 99%

“…In our previous works, we found that 3-indoleacetic acids could smoothly realize decarboxylative couplings with various nucleophilic reagents in the presence of copper salts without a need for bases and ligands (Scheme c) . Chromones are a class of important heterocyclic compounds, which widely exist in natural products and pharmaceuticals .…”

Section: Introductionmentioning

confidence: 99%

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Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones

Wen

Gao

et al. 2022

J. Org. Chem.

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Here, we describe a copper-mediated tandem decarboxylative coupling/annulation protocol of o-hydroxyaryl enaminones with 3-indoleacetic acids. A series of 3-indolmethyl-chromones were afforded in up to 97% yield. A one-pot method for 3-indolmethyl-chromones from o-hydroxy acetophenones, N, N-dimethylformamide dimethyl acetal, and 3-indoleacetic acids was also developed. Derivatization of the products was conducted to provide various indolmethyl-substituted pyrimidines. Moreover, a biological evaluation revealed that some compounds had anti-influenza viral activities.

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Section: Results and Discussionmentioning

confidence: 90%

Section: Results and Discussionmentioning

confidence: 90%

Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones

Wen

Gao

et al. 2022

J. Org. Chem.

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α‐Benzylation of Carbonyl Compounds Enabled by Synergistic Copper/Amine Catalyzed Decarboxylation of Arylacetic Acids

et al. 2023

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Herein, we report synergistic copper/amine‐catalyzed reactions for directly α‐benzylating carbonyl compounds with arylacetic acids. These reactions represent the first examples of decarboxylative oxidative synergistic transition‐metal/enamine catalysis for α‐functionalizing carbonyl compounds. The process features starting‐material availability, good functional group tolerance, mild reaction conditions, and good‐to‐excellent yields. Dibenzylated products were formed in moderate yields under slightly altered reaction conditions, and some products were transformed into 1,2,3,4‐tetrahydrocyclopenta[b]indole derivatives by acid‐catalyzed intermolecular cyclization reactions with indoles. Moreover, biological studies revealed that some products have anticancer properties and may be useful in drug‐discovery studies.

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Covalent Organic Frameworks as a Versatile Platform for Iron‐Catalyzed sp³ C−H Activation and Cross‐Coupling via Decarboxylative Oxidation

Cifuentes,

Henrique,

Ligiéro

et al. 2024

Eur J Inorg Chem

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This work demonstrates the oxidative cross‐coupling of cinnamic acids with toluene using FeCl3 immobilized on a covalent organic framework (COF) pore wall, resulting in the synthesis of 1,3‐arylpropene derivatives. This iron‐based heterogeneous catalytic system affords the desired products in moderate yields ranging from 51% to 65%. Investigations using COFs with varying pore sizes indicate that larger pores facilitate the reaction, suggesting a spatial requirement for this transformation within the catalyst. The correlation between pore size and reaction efficiency provides insights into developing tailored catalysts to match the spatial requirements of the transformation. This version emphasizes the novelty of the study and the synthesis of 1,3‐arylpropene derivatives. It also clarifies that the iron‐based heterogeneous catalytic system is responsible for the reaction. Additionally, it provides a more detailed explanation of the findings regarding pore size and spatial requirements.

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Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones

Cited by 6 publications

References 54 publications

Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones

Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones

α‐Benzylation of Carbonyl Compounds Enabled by Synergistic Copper/Amine Catalyzed Decarboxylation of Arylacetic Acids

Covalent Organic Frameworks as a Versatile Platform for Iron‐Catalyzed sp³ C−H Activation and Cross‐Coupling via Decarboxylative Oxidation

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Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones

Cited by 6 publications

References 54 publications

Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones

Copper-Mediated Cyclization of o-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones

α‐Benzylation of Carbonyl Compounds Enabled by Synergistic Copper/Amine Catalyzed Decarboxylation of Arylacetic Acids

Covalent Organic Frameworks as a Versatile Platform for Iron‐Catalyzed sp3 C−H Activation and Cross‐Coupling via Decarboxylative Oxidation

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Covalent Organic Frameworks as a Versatile Platform for Iron‐Catalyzed sp³ C−H Activation and Cross‐Coupling via Decarboxylative Oxidation