Highly substituted benzo[b]furan synthesis through substituent migration

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Heterocyclic Chemistry

Background:

• Benzofurans are important heterocyclic compounds with diverse applications.
• Existing synthesis methods for highly substituted benzofurans can be limited.
• Development of novel synthetic routes is crucial for accessing complex benzofuran structures.

Purpose of the Study:

• To disclose an unusual and efficient synthesis of highly substituted benzofurans.
• To explore a novel reaction pathway involving charge-accelerated [3,3]-sigmatropic rearrangement.
• To prepare multiaryl- and fully substituted benzofuran derivatives.

Main Methods:

• Reaction of 2,6-disubstituted phenols with alkynyl sulfoxides.
• Utilizing a charge-accelerated [3,3]-sigmatropic rearrangement mechanism.
• Employing subsequent substituent migration for structural elaboration.

Main Results:

• Successful synthesis of various highly substituted benzofurans.
• Demonstration of a unique reaction mechanism enabling complex structures.
• Preparation of multiaryl-substituted and fully substituted benzofurans.

Conclusions:

• A novel and effective benzofuran synthesis has been developed.
• The charge-accelerated [3,3]-sigmatropic rearrangement offers a unique pathway to complex benzofurans.
• This method provides access to valuable multiaryl- and fully substituted benzofuran scaffolds.