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Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights

Domenic Pace, Raphaël Robidas, Uyen P. N. Tran, Claude Y. Legault, Thành Vinh Nguyễn

2021The Journal of Organic Chemistry28 citationsDOI

Abstract

Substituted pyrans and furans are core structures found in a wide variety of natural products and biologically active compounds. Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine, a simple and inexpensive catalyst. The method described is performed under solvent-free conditions at an ambient temperature and atmosphere, thus offering a facile and practical alternative to currently available reaction protocols. A combination of experimental studies and density functional theory calculations revealed interesting mechanistic insights into this seemingly simple reaction.

Topics & Concepts

ChemistryCatalysisCombinatorial chemistryIodineOrganic chemistryComputational chemistrySolventReaction conditionsOxidative Organic Chemistry ReactionsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods
Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights | Litcius