Metal-Free Synthesis of 2<i>H</i>-Indazole Skeletons by Photochemistry or Thermochemistry

Zhang, Gan; Zhang, Yicheng; Li, Pinhua; Zhou, Chao; Wang, Min; Wang, Lei

doi:10.1021/acs.joc.3c01091

Cited by 5 publications

(1 citation statement)

References 55 publications

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“…In the past two decades, the organic synthetic community has recognized the potential of a fundamentally different approach to visible-light-promoted transformations enabled by electron donor−acceptor (EDA) complexes, as it does not rely on the use of additional photocatalysts . This strategy involves the combination of electron acceptor substrate A and donor molecule D (acting as Lewis acid and base, respectively) to form new EDA complexes in the ground state.…”

Section: Introductionmentioning

confidence: 99%

EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

Zhang,

Guo,

Yang

et al. 2024

J. Org. Chem.

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A photocatalyst-free and EDA complex-enabled radical cascade cyclization reaction of inactive alkenes with bromodifluoroacetamides was reported for the divergent synthesis of fluorine-containing tetralones and quinazolinones. In this transformation, persulfates as electron donors and difluoro bromamide as electron acceptors generate the EDA complex. This is a promising photochemical method with advantages such as mild reaction conditions, simple operation, being metal-free, and excellent functional group tolerance.

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Section: Introductionmentioning

confidence: 99%

EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

Zhang,

Guo,

Yang

et al. 2024

J. Org. Chem.

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An Electrochemical Oxo‐amination of 2H‐Indazoles: Synthesis of Symmetrical and Unsymmetrical Indazolylindazolones

Mondal,

Ghosh,

Hajra

2024

Chemistry A European J

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We have established a supporting‐electrolyte free electrochemical method for the synthesis of indazolylindazolones through oxygen reduction reaction (eORR) induced 1,3‐oxo‐amination of 2H‐indazoles where 2H‐indazole is used as both aminating agent as well as the precursor of indazolone. Moreover, we have merged indazolone and indazole to get unsymmetrical indazolylindazolones through direct electrochemical cross‐dehydrogenative coupling (CDC). This exogenous metal‐, oxidant‐ and catalyst‐free protocol delivered a number of multi‐functionalized products with high tolerance of diverse functional groups.

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Recent Developments in the Photochemical Reactions of N‐Heterocyclic Compounds

Barathkumar,

Gupta,

Nagarajan

2024

Eur J Org Chem

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The adoption of clean and renewable light sources is becoming increasingly prevalent in organic synthesis due to their welfare, workability and economic benefits. In recent times, photo‐redox catalysis has emerged as a valuable tool in organic transformations owing to its environmentally friendly nature and utilization of abundant resources. Since harmful or polluting reagents are not needed for the organic photochemical reactions, these reactions provide insights into sustainable processes and green chemistry. N‐Heterocyclic compounds (NHC’s) constitute fundamental structural motifs in numerous organic compounds and are widely encountered in natural products and pharmaceuticals with diverse biological activities. Consequently, investigations into the synthesis and modification of these NHC’s such as indole, carbazole, benzimidazole, quinoline, isoquinoline and pyridine hold particular significance for chemists and pharmacologists. This review provides an overview of the impact of photocatalysis on synthesis of NHC’s and their modification from 2019 to 2024. These transformations are achieved through the utilization of both metal photocatalysts (e.g., Ir, Pd, Co, Gd etc.) and non‐metallic photocatalysts (e.g., Eosin‐Y, 4CzIPN, Mes‐Acr+ClO4‐ etc.), or even without the necessity of photocatalysts. It is anticipated that this review will serve as a valuable resource for researchers delving into the promising realm of photocatalyzed transformations.

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Metal-Free Synthesis of 2H-Indazole Skeletons by Photochemistry or Thermochemistry

Cited by 5 publications

References 55 publications

EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

An Electrochemical Oxo‐amination of 2H‐Indazoles: Synthesis of Symmetrical and Unsymmetrical Indazolylindazolones

Recent Developments in the Photochemical Reactions of N‐Heterocyclic Compounds

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Metal-Free Synthesis of 2H-Indazole Skeletons by Photochemistry or Thermochemistry

Cited by 5 publications

References 55 publications

EDA Complex-Enabled Annulation to Access CF2-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

EDA Complex-Enabled Annulation to Access CF2-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

An Electrochemical Oxo‐amination of 2H‐Indazoles: Synthesis of Symmetrical and Unsymmetrical Indazolylindazolones

Recent Developments in the Photochemical Reactions of N‐Heterocyclic Compounds

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EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors