Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds

Herein, a mechanochemically triggered C–H arylation of coumarins, quinoline-N-oxides, and uracil molecules with aryl thianthrenium salts is described. Aryl thianthrenium salts are primarily acknowledged for their expedient reusability and adherence to atom economy principles. Mechanistic studies suggested that mechanical stress promoted the homolytic scission of C–S bond of aryl thianthrenium salts, forming aryl radical intermediate. Later, the aryl radical intermediate is engaged in addition reaction with the above heterocycles, leading to the desired products in good yields. This versatile protocol accommodates a wide range of functional groups and facilitates the synthesis of bioactive compounds and drug molecules.

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Publication Details

Journal
ACS Sustainable Chemistry & Engineering
Published
2024-08-15
DOI
https://doi.org/10.1021/acssuschemeng.4c03163
Citations
11
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.75

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article

Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds

Raman Kumar, Anuj Sharma, Anoop Sharma
11 citations
ACS Sustainable Chemistry & Engineering
Radical Photochemical Reactions
2.75
article

Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds

Raman Kumar, Anuj Sharma, Anoop Sharma
article en
11 citations

Abstract

Herein, a mechanochemically triggered C–H arylation of coumarins, quinoline-N-oxides, and uracil molecules with aryl thianthrenium salts is described. Aryl thianthrenium salts are primarily acknowledged for their expedient reusability and adherence to atom economy principles. Mechanistic studies suggested that mechanical stress promoted the homolytic scission of C–S bond of aryl thianthrenium salts, forming aryl radical intermediate. Later, the aryl radical intermediate is engaged in addition reaction with the above heterocycles, leading to the desired products in good yields. This versatile protocol accommodates a wide range of functional groups and facilitates the synthesis of bioactive compounds and drug molecules.

ACS Sustainable Chemistry & EngineeringVol. 12(34)
Indian Institute of Technology Roorkee (IN)
University Grants Committee, Science and Engineering Research Board
Openalex Percentile: Top 10%
Radical Photochemical Reactions
2.75
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Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds — Raman Kumar, Anuj Sharma, et al. · ACS Sustainable Chemistry & Engineering (2024) | TGRS Research Map | TGRS