Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Hypervalent aryliodoniums are effective arylating agents, superior to aryl halides under mild conditions.
• Acyclic aryliodoniums suffer from poor reaction economy due to wasted aryl iodide byproducts.
• Cyclic aryliodoniums present an advantage in reaction economy and are key for cascade reactions.

Purpose of the Study:

• To summarize recent advancements in cyclic aryliodoniums.
• To cover the design of new aryliodonium species and their synthetic applications.
• To highlight their role in constructing complex molecules and as organocatalysts.

Main Methods:

• Preparation of diphenyl, heterocyclic, and monoaryl iodoniums.
• Utilizing arylation reactions coupled with domino reactions for polycycle synthesis.
• Systematic discussion of biaryl construction, including axial atropisomers.

Main Results:

• Demonstrated efficient synthesis of polycyclic structures with potential pharmaceutical properties.
• Showcased the construction of biaryls, including challenging axial atropisomers.
• Highlighted the novel application of cyclic aryliodoniums as halogen-bonding organocatalysts.

Conclusions:

• Cyclic aryliodoniums are versatile reagents with significant advantages over acyclic counterparts.
• Their application in cascade reactions and catalysis opens new avenues for complex molecule synthesis.
• Continued research in cyclic aryliodoniums promises further innovation in organic synthesis.