Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF<sub>2</sub>SO<sub>2</sub>Ph Reagent

Li, Shali; Wang, Xiu; Yang, Yide; Ni, Chuanfa; Hu, Jinbo

doi:10.1021/acs.orglett.3c04116

Org. Lett.

2024

DOI: 10.1021/acs.orglett.3c04116

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Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF₂SO₂Ph Reagent

Shali Li,

Xiu Wang,

Yide Yang

et al.

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Cited by 4 publications

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Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Wu,

Goujon,

Pan

et al. 2024

Angewandte Chemie

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Benzo[1,3,2]dithiazole‐1,1,3‐trioxides are bench‐stable and easy‐to‐use reagents. In photoredox catalysis, they generate methyl and perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, and N‐Ts acrylamide. As byproduct, a salt is formed which can be regenerated to the original methylating agent. Flow chemistry provides an option for reaction scale‐up further underscoring the synthetic usefulness of these methylation reagents. Mechanistic investigations suggest a single‐electron transfer (SET) pathway induced by photoredox catalysis.

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Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Wu,

Goujon,

Pan

et al. 2024

Angewandte Chemie

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Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Wu,

Goujon,

Pan

et al. 2024

Angew Chem Int Ed

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Photocatalyzed Imino-Difluoromethylation of Alkenes with Bifunctional Oxime Esters

Chen,

Yang,

et al. 2024

J. Org. Chem.

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Herein, we report a simple and versatile difluoromethylene-imide reaction in which a series of olefins can undergo a difluoromethylenimine reaction under photocatalytic conditions through an energy transfer (EnT) process. The reaction has mild conditions and a wide range of applicability. We successfully synthesized 27 molecules containing difluoromethylene units, featuring easily accessible starting materials and operational simplicity.

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Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF₂SO₂Ph Reagent

Cited by 4 publications

References 48 publications

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Photocatalyzed Imino-Difluoromethylation of Alkenes with Bifunctional Oxime Esters

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Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF2SO2Ph Reagent

Cited by 4 publications

References 48 publications

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Photocatalyzed Imino-Difluoromethylation of Alkenes with Bifunctional Oxime Esters

Contact Info

Product

Resources

About

Divergent Generation of the Difluoroalkyl Radical and Difluorocarbene via Selective Cleavage of C–S Bonds of the Sulfox-CF₂SO₂Ph Reagent