Visible-light photoredox-catalyzed radical aryldifluoromethylation of <i>N</i>-arylacrylamides with <i>S</i>-(difluoromethyl)sulfonium salt

Zhao, Ya-Shi; Huang, Sheng-Jie; Gu, Yuan-Qing; Liu, Guokai

doi:10.1039/d3ob00488k

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00488k

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Visible-light photoredox-catalyzed radical aryldifluoromethylation of N-arylacrylamides with S-(difluoromethyl)sulfonium salt

Ya-Shi Zhao

Sheng-Jie Huang

Yuan-Qing Gu

et al.

Abstract: A facile and highly efficient visible-light photoredox-catalyzed protocol for aryldifluoromethylation of arcylamides was developed using S-(difluoromethyl)sulfoniu salt as difluoromethyl source. With this method, pharmaceutically interesting CF2H-containing oxindoles were readily accessed...

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2024

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Cited by 4 publications

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Introduction of Difluoromethyl Through Radical Pathways

Li,

Song

2024

Eur J Org Chem

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During the past decade, radical difluoromethylation has received much attention and rapid developments for its mild reaction conditions and good functional group compatibilities. A diverse array of difluoromethyl radical precursors and corresponding radical reactions have been disclosed. This review summarizes and discusses the recent progress on the radical difluoromethylation reactions, which are organized according to the protocols of generating difluoromethyl radical.

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Introduction of Difluoromethyl Through Radical Pathways

Li,

Song

2024

Eur J Org Chem

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Visible‐Light‐Mediated Oxidative Desulfurization‐Oxygenation in Cyclic Thio‐Amide

Das,

Mondal

et al. 2024

ChemistrySelect

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Visible‐light assisted a very simple and mild protocol for photocatalytic oxidative transformation of thioamide to amide group has been realized in cyclic system. For this purpose 5‐arylalkylidene‐rhodanine derivatives were chosen as model substrates to afford thiazolidine‐2,4‐diones. Light mediated reactions are intrinsically beneficial, since activation occurs by cleanest energy source light. Here K2S2O8 is used as terminal oxidant which does not leave any hazardous and corrosive waste to discard after the reaction fostering the practices of green chemistry. This is the first report of conversion of thioxo group in rhodanine derivatives into the corresponding oxygen analogue by visible light photo‐catalytic method. The reaction was very general since various 5‐arylalkylidene‐rhodanines underwent the reaction smoothly affording high product yields. Moreover, the broadness of this protocol was further established by applying this reaction on other systems like 3,4‐dihydropyrimidine‐2(1H)‐(thio)ones.

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General radical difluoromethylation using difluoroacetic anhydride via photoredox catalysis

He,

Yang,

Zhang

et al. 2024

Sci. China Chem.

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Visible-light photoredox-catalyzed radical aryldifluoromethylation of N-arylacrylamides with S-(difluoromethyl)sulfonium salt

Cited by 4 publications

References 46 publications

Introduction of Difluoromethyl Through Radical Pathways

Introduction of Difluoromethyl Through Radical Pathways

Visible‐Light‐Mediated Oxidative Desulfurization‐Oxygenation in Cyclic Thio‐Amide

General radical difluoromethylation using difluoroacetic anhydride via photoredox catalysis

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