Copper-promoted indirect trifluoromethylthiolation of sulfuryl chloride with TMSCF<sub>3</sub>: facile access to trifluoromethyl thioethers

Zheng, Changge; Zhao, Kui; Jiang, Chao; Feng, Ruilong; Li, Chunxiang; Chen, X; Chen, Wei; Gong, X.; Hong, Jianquan

doi:10.1039/d3nj01319g

New J. Chem.

2023

DOI: 10.1039/d3nj01319g

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Copper-promoted indirect trifluoromethylthiolation of sulfuryl chloride with TMSCF₃: facile access to trifluoromethyl thioethers

Changge Zheng¹,

Kui Zhao²,

Chao Jiang³

et al.

Abstract: A simple and practical synthetic method for trifluoromethyl thioethers through copper-promoted indirect trifluoromethylthiolation has been developed. The reaction of sulfuryl chloride with commercial Ruppert-Prakash reagent TMSCF3 is performed under mild...

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Cited by 2 publications

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Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

An,

Zeng,

Tang

et al. 2023

Eur J Org Chem

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Efficient approaches to perfluoroalkyl/alkenyl aryl sulfides were accomplished by a C−S coupling reaction under mild conditions. Hexafluoropropylene dimer was employed as a versatile building block for the perfluoroalkylation and perfluoroalkenylation of thiophenol. The application of the synthetic strategy was demonstrated by the high‐yield transformation of a broad range of aryl derivatives. A plausible mechanistic explanation was proposed to elaborate the differences between the two reaction pathways. The methodology provides straightforward and convenient access to aryl sulfides constituting C6 perfluoroalkyl and perfluoroalkenyl substituents.

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Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

An,

Zeng,

Tang

et al. 2023

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Electrochemical Trifluoromethylthiolation/Cyclization of N-Arylacrylamides with AgSCF₃: Access to SCF₃-Containing Oxindoles

Wang,

Wang

et al. 2024

J. Org. Chem.

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Copper-promoted indirect trifluoromethylthiolation of sulfuryl chloride with TMSCF₃: facile access to trifluoromethyl thioethers

Abstract: A simple and practical synthetic method for trifluoromethyl thioethers through copper-promoted indirect trifluoromethylthiolation has been developed. The reaction of sulfuryl chloride with commercial Ruppert-Prakash reagent TMSCF3 is performed under mild...

Cited by 2 publications

References 53 publications

Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

Electrochemical Trifluoromethylthiolation/Cyclization of N-Arylacrylamides with AgSCF₃: Access to SCF₃-Containing Oxindoles

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Copper-promoted indirect trifluoromethylthiolation of sulfuryl chloride with TMSCF3: facile access to trifluoromethyl thioethers

Abstract: A simple and practical synthetic method for trifluoromethyl thioethers through copper-promoted indirect trifluoromethylthiolation has been developed. The reaction of sulfuryl chloride with commercial Ruppert-Prakash reagent TMSCF3 is performed under mild...

Cited by 2 publications

References 53 publications

Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

Electrochemical Trifluoromethylthiolation/Cyclization of N-Arylacrylamides with AgSCF3: Access to SCF3-Containing Oxindoles

Contact Info

Product

Resources

About

Copper-promoted indirect trifluoromethylthiolation of sulfuryl chloride with TMSCF₃: facile access to trifluoromethyl thioethers

Electrochemical Trifluoromethylthiolation/Cyclization of N-Arylacrylamides with AgSCF₃: Access to SCF₃-Containing Oxindoles