Efficient synthesis of 2-benzofuranyl C-glycosides by one-pot cascade reaction of sugar alkynes and substituted 2-iodophenols

Abstract

2-Benzofuranyl C-glycosides were synthesized in good to excellent yields by one-pot cascade reaction of terminal sugar alkynes and substituted 2-iodophenols. The products have wide structural diversity and potential biological activity. This new synthetic method is general, mild, and efficient. Thirty-seven examples have been given. The structurally diverse terminal sugar alkynes included pyranosides, furanosides, and acyclic sugars with sensitive and bulky protecting groups. The substituted 2-iodophenols contained electron-donating, electron-withdrawing, and electron-neutral substituents. The mechanism for the formation of the products has been proposed.

Graphical Abstract

Keywords:

• Aryl C-glycoside
• 2-substituted benzofuran
• sugar
• alkyne

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

We gratefully acknowledge the National Natural Science Foundation of China (No. 21772180) for financial support.