Decarboxylative Iodination of Coumarin‐3‐carboxylic Acids: A Facile Access to 3‐Iodocoumarins

A straightforward protocol for the direct conversion of readily available coumarin‐3‐carboxylic acids to the corresponding 3‐iodocoumarins is described herein. Heating acetonitrile solution of coumarin‐3‐carboxylic acids, molecular iodine and potassium hydrogen phosphate resulted in the decarboxylat...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2024-12, Vol.13 (12), p.n/a
Main Authors: Thotathil, Vandana, Sidiq, Naheed, Idoudi, Souha, Al‐Zoubi, Raed M., Shkoor, Mohanad, Dawoud Bani‐Yaseen, Abdulilah
Format: Article
Language:English
Subjects:
3-Bromocoumarin
3-Iodocoumarin
Acetonitrile
Carboxylic acids
Coumarin
Decarboxylation
Direct conversion
Halogenation
Iodination
Iodine
Organic compounds
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Summary:A straightforward protocol for the direct conversion of readily available coumarin‐3‐carboxylic acids to the corresponding 3‐iodocoumarins is described herein. Heating acetonitrile solution of coumarin‐3‐carboxylic acids, molecular iodine and potassium hydrogen phosphate resulted in the decarboxylative iodination of coumarin‐3‐carboxylic acids via radical mechanism. Various electron rich and electron poor coumarin‐3‐carboxylic acids were compatible with the established reaction conditions and consequently afforded the corresponding 3‐iodocoumarins in (46–93 %) reaction yields with minimum purification efforts. The formed products serve as valuable precursors to streamline more complex organic compounds incorporating coumarin core. 3‐Iodocoumarins are valuable precursors to access more complex coumarins. We disclosed a facile route for the direct synthesis of 3‐Iodocoumarins from the readily available coumarins‐3‐carboxylic acids using molecular iodine. Several 3‐Iodocoumarins were prepared with satisfacotry yields and minimum purification efforts.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202400308