Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

King, Eric R.; Tarrago, Maxime; Ghosh, Avipsa

doi:10.1039/d3cy01394d

Catal. Sci. Technol.

2023

DOI: 10.1039/d3cy01394d

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Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

Eric R. King,

Maxime Tarrago,

Avipsa Ghosh

Abstract: We report the development of a nickel-catalyzed, photoredox-based approach for the (trifluoromethyl)thiolation of alkenyl iodides to access diverse and biologically relevant alkenyl sulfides under mild and air-tolerant conditions.

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2024

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Cited by 2 publications

References 56 publications

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Efficient synthesis of SCF₃-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Wang,

Liu,

Yang

et al. 2024

Org. Biomol. Chem.

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Efficient synthesis of SCF₃-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Wang,

Liu,

Yang

et al. 2024

Org. Biomol. Chem.

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Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

Li,

Song,

Zhang

et al. 2024

Synthesis

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Photoredox catalysis has evolved into a widely used method and has fostered the extensive utilization of radical coupling partners in organic synthesis over the past years. The integration of visible-light photocatalysis into fluorine chemistry has achieved many important transformations for radical fluorination and fluoroalkylation, which usually proceeded smoothly under mild conditions with simple oxidants or reductants, exhibiting a broad range of substrates and excellent functional group tolerance. In this review, we highlight the photoredox-catalyzed procedures for the trifluoromethylthiolation and trifluoromethylselenolation reactions as well as their possible mechanisms. The ease and environment-friendliness of shuttling electrons back and forth to substrates or intermediates, and selectively transferring energy through visible-light-absorbing catalysts or EDA complexes holds promise to improve the trifluoromethylthiolation and trifluoromethylselenolation in radical chemistry.

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Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

Abstract: We report the development of a nickel-catalyzed, photoredox-based approach for the (trifluoromethyl)thiolation of alkenyl iodides to access diverse and biologically relevant alkenyl sulfides under mild and air-tolerant conditions.

Cited by 2 publications

References 56 publications

Efficient synthesis of SCF₃-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Efficient synthesis of SCF₃-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

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Metallaphotoredox catalysis enables facile (trifluoromethyl)thiolation of alkenyl iodides

Abstract: We report the development of a nickel-catalyzed, photoredox-based approach for the (trifluoromethyl)thiolation of alkenyl iodides to access diverse and biologically relevant alkenyl sulfides under mild and air-tolerant conditions.

Cited by 2 publications

References 56 publications

Efficient synthesis of SCF3-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Efficient synthesis of SCF3-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Progress in Photocatalyzed Trifluoromethylthiolation and Trifluoromethylselenolation Reactions

Contact Info

Product

Resources

About

Efficient synthesis of SCF₃-containing 3-alkenylquinoxalinones via three-component radical cascade reaction

Efficient synthesis of SCF₃-containing 3-alkenylquinoxalinones via three-component radical cascade reaction