Modular access to diarylmethyl sulfonamides via visible light-promoted cross-coupling reactions

Area of Science:

• Organic Chemistry
• Photocatalysis
• Synthetic Methodology

Background:

• Sulfonamides are crucial in medicinal chemistry and materials science.
• Efficient synthesis of diarylmethyl sulfonamides remains a challenge.

Purpose of the Study:

• To develop a novel, mild, and metal-free method for synthesizing diarylmethyl sulfonamide derivatives.
• To explore the scope and limitations of the new protocol.

Main Methods:

• Visible-light-induced photocatalysis using rhodamine 6G.
• Sulfamoylation of para-quinone methides with sulfamoyl chlorides.
• Metal-free reaction conditions.

Main Results:

• Successful preparation of diarylmethyl sulfonamide derivatives in moderate to high yields.
• Excellent functional group tolerance observed.
• Mechanism involves excited photocatalyst quenching and radical-radical cross-coupling.

Conclusions:

• The developed method is efficient and versatile for diarylmethyl sulfonamide synthesis.
• The protocol offers a sustainable and mild alternative to existing methods.
• This work provides a new pathway for accessing valuable sulfonamide compounds.