Synthesis of Complex Diarylamines through a Ring-Opening Difunctionalization Strategy

Area of Science:

• Organic Chemistry
• Medicinal Chemistry

Background:

• Cyclic amines are vital scaffolds in drug discovery.
• Expanding their properties is key to developing new therapeutics.

Purpose of the Study:

• To develop a novel synthetic strategy for diarylamines.
• To enable skeletal diversification of cyclic amines for drug discovery applications.

Main Methods:

• Diarylation and skeletal diversification of unstrained cyclic amines.
• Synthesis of amino-substituted diaryliodonium salts.
• Atom-efficient one-pot N-arylation/ring opening with nucleophiles.

Main Results:

• A wide variety of highly functionalized diarylamines were synthesized.
• The method demonstrated high functional group tolerance with over 20 nucleophiles.
• Efficient late-stage functionalization of natural products and pharmaceuticals was achieved.

Conclusions:

• The developed method provides access to diverse diarylamines with potential in drug discovery.
• The strategy is versatile, enabling modifications of complex molecules and pharmaceuticals.