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

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 m...

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Veröffentlicht in:Journal of organic chemistry 2021-06, Vol.86 (12), p.8154-8171
Hauptverfasser: Pace, Domenic P, Robidas, Raphaël, Tran, Uyen P. N, Legault, Claude Y, Nguyen, Thanh Vinh
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00608