4.7 Article

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

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 12, 页码 8154-8171

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00608

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资金

  1. Australian Research Council [FT180100260, DP200100063]
  2. NSERC
  3. Australian Research Council [FT180100260, DP200100063] Funding Source: Australian Research Council

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A practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine has been reported, offering a facile alternative under solvent-free conditions at ambient temperature and atmosphere. Mechanistic insights into this seemingly simple reaction were revealed through a combination of experimental studies and density functional theory calculations.
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.

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