Selectivity Control in Visible-Light-Induced Three-Component Cascade Thiolation-Difluoroalkylation of Alkynes
Mengqi Zhu1, Huawen Huang1, Yun Wang1
1College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, China.
A new visible-light reaction enables regioselective thiolation-difluoroalkylation of alkynes. This method efficiently synthesizes gem-difluoroalkyl thioethers from diverse starting materials.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Synthetic Methodology
Background:
- Visible-light photocatalysis offers a sustainable approach to organic synthesis.
- Developing regioselective methods for complex molecule construction is crucial.
- Difluoroalkylation and thiolation are important transformations in medicinal chemistry.
Purpose of the Study:
- To report a novel visible-light-induced three-component reaction for the synthesis of gem-difluoroalkyl thioethers.
- To achieve regioselective thiolation-difluoroalkylation of alkynes.
- To explore the compatibility of the reaction with various substrates.
Main Methods:
- Visible-light irradiation.
- Three-component reaction involving alkynes, trifluoromethylarenes, and thiols.
- Photocatalytic system optimization.
Main Results:
- Successful regioselective synthesis of gem-difluoroalkyl thioethers.
- Demonstrated compatibility with a wide range of unactivated alkynes, trifluoromethylarenes, and thiols.
- Established a reaction cascade involving sequential thiolation and difluoroalkylation.
Conclusions:
- A mild and efficient visible-light-induced method for synthesizing gem-difluoroalkyl thioethers has been developed.
- The reaction exhibits excellent regioselectivity, placing the acetylene substituent distal to the sulfur atom.
- This methodology provides a valuable tool for accessing functionalized organofluorine compounds.
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