Diaryliodonium Salts Enabled Arylation, Arylocyclization, and Aryl-Migration

Area of Science:

• Organic Chemistry
• Synthetic Methodology

Background:

• Diaryliodonium salts are versatile reagents in organic synthesis.
• Dual activation strategies involving C-I and ortho C-H bonds offer unique reactivity pathways.

Purpose of the Study:

• To summarize research on synthetic methodology utilizing diaryliodonium salts.
• To explore the reactivity of functionalized diaryliodonium salts in various organic transformations.
• To discuss reaction mechanisms involving transition metal catalysis and metal-free conditions.

Main Methods:

• Employing a dual activation strategy of C-I and ortho C-H bonds.
• Introducing vicinal functional groups at ortho-positions of diaryliodonium salts.
• Investigating reactions under transition metal (e.g., palladium) catalysis and transition-metal-free conditions.

Main Results:

• Demonstrated unique reactivities of functionalized diaryliodonium salts.
• Achieved various processes including arylation, diarylation, cascade annulation, benzocyclization, arylocyclization, and intramolecular aryl migration.
• Explored diverse reaction mechanisms.

Conclusions:

• Diaryliodonium salts, particularly those with ortho-functionalization, are powerful tools for synthetic methodology.
• The developed methods offer efficient access to complex molecular architectures.
• Understanding the mechanistic pathways is crucial for further synthetic advancements.