Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)<sub>2</sub> and CHI<sub>3</sub> under Ambient Conditions

We have developed a mild and practical synthesis of primary, secondary and tertiary alkyl iodides by iododecarboxylation (decarboxylative iodination) of the corresponding carboxylic acids using (diacetoxyiodo)benzene and iodoform under ambient conditions. The method does not require heating or intense light irradiation and can be used to install iodine at the bridgehead position of strained cycloalkanes, as well as in a variety of alkanes with complex frameworks/functionalities.

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Publication Details

Journal
Organic Letters
Published
2025-04-21
DOI
https://doi.org/10.1021/acs.orglett.5c00924
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)2 and CHI3 under Ambient Conditions

Kazunori Miyamoto, Tadafumi Matsunaga, Shinichiro Kamino, Marie Kubota et al.
Organic Letters
Oxidative Organic Chemistry Reactions
article

Iodo-decarboxylation of Aliphatic Carboxylic Acids with PhI(OAc)2 and CHI3 under Ambient Conditions

Kazunori Miyamoto, Tadafumi Matsunaga, Shinichiro Kamino, Marie Kubota, Kyoka Sakamoto, Masanobu Uchiyama
article en

Abstract

We have developed a mild and practical synthesis of primary, secondary and tertiary alkyl iodides by iododecarboxylation (decarboxylative iodination) of the corresponding carboxylic acids using (diacetoxyiodo)benzene and iodoform under ambient conditions. The method does not require heating or intense light irradiation and can be used to install iodine at the bridgehead position of strained cycloalkanes, as well as in a variety of alkanes with complex frameworks/functionalities.

Organic LettersVol. 27(17)
Aichi Gakuin University (JP), Keio University (JP), The University of Tokyo (JP)
Naito Foundation, Asahi Glass Foundation, Uehara Memorial Foundation, Nagase Science Technology Foundation, Japan Society for the Promotion of Science, Core Research for Evolutional Science and Technology
Openalex Percentile: Top 94%
Oxidative Organic Chemistry Reactions
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