Nucleophilic functionalization of thianthrenium salts under basic conditions

Area of Science:

• Organic Chemistry
• Synthetic Methodology
• Catalysis

Background:

• S-(alkyl)thianthrenium salts are valuable for functionalizing alcohols.
• Current methods often require transition metal catalysts or visible light irradiation.
• A need exists for more efficient and accessible synthetic routes.

Purpose of the Study:

• To develop a direct thioetherification/amination reaction of thianthrenium salts.
• To achieve this transformation under metal-free conditions.
• To offer a simpler and broader alternative to existing methods.

Main Methods:

• Utilizing S-(alkyl)thianthrenium salts as key reagents.
• Performing direct thioetherification and amination reactions.
• Operating under metal-free and visible light-free conditions.

Main Results:

• Successful direct thioetherification and amination of thianthrenium salts achieved.
• The reaction proceeds efficiently without transition metal catalysts or visible light.
• Demonstrated good functional group tolerance and operational simplicity.

Conclusions:

• A novel metal-free strategy for thianthrenium salt functionalization has been established.
• This method provides a versatile and straightforward approach for synthesizing thioethers and amines.
• The developed protocol broadens the scope of accessible substrates for these important transformations.