Acyl Iodide Synthesis from Carboxylic Acids Using a Novel Ph2P(O)H‐I2 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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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2024-10, Vol.9 (39), p.n/a
Main Authors: Fujiwara, Kohsuke, Kawaguchi, Shin‐ichi, Yamamoto, Yuki, Gonda, Yuhei, Ogawa, Akiya
Format: Article
Language:English
Subjects:
Acyl iodides
Acylation
Carboxylic acids
Iodine
One‐pot reaction
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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 I2 and diphenylphosphine oxide (Ph2P(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. A binary system combining diiodine and diphenylphosphine oxide has been developed to provide a simple method for the synthesis of acyl iodides from carboxylic acids. By reacting amines, alcohols, and thiols with the acyl iodides generated, the corresponding amides, esters, and thioesters, respectively, can be synthesized in a one‐pot manner.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202404567