Direct Synthesis of Diaryl Sulfoxides from Arylboronic Acids

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Synthetic Chemistry

Background:

• Sulfoxide compounds are crucial in pharmaceutical development.
• Existing synthetic methods for diaryl sulfoxides can be limited in scope or require harsh conditions.

Purpose of the Study:

• To develop a novel, efficient, and mild synthetic strategy for diaryl sulfoxides.
• To provide a versatile method for accessing both symmetrical and unsymmetrical diaryl sulfoxides.

Main Methods:

• An acid-promoted reaction utilizing commercially available arylboronic acids.
• Employing trifluoroacetic acid and diethylaminosulfur trifluoride (DAST) as key reagents.
• Mild reaction conditions with no requirement for bases or external oxidants.

Main Results:

• Successful synthesis of over 35 examples of diaryl sulfoxides.
• Achieved good to excellent yields, up to 90%.
• Demonstrated good functional group tolerance and a simple operational procedure.

Conclusions:

• The reported method provides a straightforward and effective route to valuable diaryl sulfoxides.
• This strategy is advantageous for pharmaceutical synthesis due to its mild conditions and efficiency.
• Mechanistic studies were conducted to understand the reaction pathway.