A simple and efficient synthesis of 2,3-diarylnaphthofurans using sequential hydroarylation/Heck oxyarylation

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Naphthofurans are important heterocyclic compounds with diverse applications.
• Efficient synthesis of substituted naphthofurans remains a challenge.

Purpose of the Study:

• To develop an efficient and simple synthetic strategy for 2,3-diarylnaphthofurans.
• To explore a sequential one-pot reaction combining hydroarylation and Heck-oxyarylation.

Main Methods:

• Sequential hydroarylation of naphthols and alkynes catalyzed by Indium(III) triflate (In(OTf)3).
• Microwave irradiation to accelerate the hydroarylation step.
• One-pot Heck-oxyarylation of the intermediate 1-substituted-α-hydroxy styrenes.

Main Results:

• Successful synthesis of various 2,3-diarylnaphthofurans.
• High efficiency and simplicity of the developed sequential strategy.
• The reaction proceeds under mild conditions with microwave assistance.

Conclusions:

• The developed method provides a facile and efficient route to 2,3-diarylnaphthofurans.
• This strategy is a valuable addition to the synthetic chemist's toolkit for accessing complex heterocyclic structures.