Acyl Iodide Synthesis from Carboxylic Acids Using a Novel Ph 2 P(O)H‐I 2 Binary System and Its Application to Facile Preparation of Amides, Esters, and Thioesters

Acyl iodides are expected to be excellent acylating agents due to the low bond dissociation energy of the carbon–iodine bond and the high capability of iodine as a leaving group. Unfortunately, the preparative methods for acyl iodides directly from carboxylic acids are rather limited. In this work,...

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Published in:ChemistrySelect (Weinheim) 2024-10, Vol.9 (39)
Main Authors: Fujiwara, Kohsuke, Kawaguchi, Shin‐ichi, Yamamoto, Yuki, Gonda, Yuhei, Ogawa, Akiya
Format: Article
Language:English
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Summary:Acyl iodides are expected to be excellent acylating agents due to the low bond dissociation energy of the carbon–iodine bond and the high capability of iodine as a leaving group. Unfortunately, the preparative methods for acyl iodides directly from carboxylic acids are rather limited. In this work, we found that a novel binary system combining I 2 and diphenylphosphine oxide (Ph 2 P(O)H) provides a simple method for the preparation of acyl iodides from carboxylic acids. Furthermore, the subsequent one‐pot reaction with appropriate nucleophiles, such as amines, alcohols, and thiols, afforded the corresponding amides, esters, and thioesters, respectively, in good to excellent yields.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202404567