Synthesis of 3-Chalcogenylated Benzo[b]furans Enabled by a Multicomponent Reagent System

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Heterocyclic Chemistry

Background:

• Benzo[b]furans are important heterocyclic compounds with diverse biological activities.
• Efficient synthetic methods for functionalized benzo[b]furans are crucial for drug discovery and materials science.

Purpose of the Study:

• To develop a novel one-pot synthetic strategy for 3-chalcogenylated benzo[b]furans.
• To explore the compatibility of various substituted 2-alkynylanisole substrates with the developed protocol.

Main Methods:

• A multicomponent reagent system involving 4-FPhI, mCPBA, (COCl)2, and RSSR or RSeSeR was employed.
• The reaction was conducted under mild conditions for the synthesis of benzo[b]furan derivatives.

Main Results:

• The one-pot synthesis successfully afforded structurally diverse 3-chalcogenylated benzo[b]furans.
• A range of 2-alkynylanisole substrates with different substituents were compatible, yielding products in moderate to excellent yields.
• Control experiments indicated the formation of electrophilic RSeCl/RSCl species initiating the cyclization and chalcogenylation.

Conclusions:

• The developed multicomponent reagent system provides an efficient and mild route to 3-chalcogenylated benzo[b]furans.
• The protocol demonstrates broad substrate scope and good yields, making it valuable for synthesizing diverse benzo[b]furan derivatives.