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

Domenic P. Pace, Raphaël Robidas, Uyen P. N. Tran, Claude Y. Legault* and Thanh Vinh Nguyen*

*Université de Sherbrooke, Québec J1K 2R1, Canada; University of New South Wales, Sydney, New South Wales 2052, Australia, Email: claude.legaultusherbrooke.ca, t.v.nguyenunsw.edu.au

D. P. Pace, R. Robidas, U. P. N. Tran, C. Y. Legault, T. V. Nguyen, J. Org. Chem., 2021, 86, 8154-8171.

DOI: 10.1021/acs.joc.1c00608 (free Supporting Information)



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Abstract

Molecular iodine catalyzes practical and mild syntheses of substituted pyrans and furans under solvent-free conditions at 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.

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Proposed Catalytic Cycle Supported by DFT Calculations (Free Energies Reported in kcal/mol)



Key Words

3,4-dihydro-2H-pyrans, furans, 2,3-dihydrofurans


ID: J42-Y2021