Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Thiomethylation is a crucial transformation in organic synthesis.
• Existing methods for thiomethylation often face limitations in substrate scope and reaction conditions.

Purpose of the Study:

• To develop an efficient and versatile method for the thiomethylation of aryl chlorides.
• To enable late-stage functionalization of complex molecules.

Main Methods:

• Utilized a combination of masked inorganic sulfur and dimethyl carbonate.
• Investigated the cross-coupling reaction of aryl chlorides.

Main Results:

• Successfully achieved thiomethylation of aryl chlorides.
• Demonstrated the method's efficacy on nucleosides, pharmaceuticals, and herbicides.
• Achieved high yields with lower catalyst loading and scalability to multigram scale.

Conclusions:

• The developed protocol offers a powerful and practical strategy for thiomethylation.
• The method is applicable to a wide range of challenging substrates.
• This approach facilitates efficient synthesis of thiomethylated compounds.