Cationic Iridium-Catalyzed Decarboxylation of Aromatic Carboxylic Acids

Reina Nonami; Yu Kishino; Tomokazu Yamasaki; Kazuya Kanemoto; Kento Iwai; Nagatoshi Nishiwaki; Kazutaka Shibatomi; Tomohiko Shirai

doi:10.1002/asia.202300533

Cationic Iridium-Catalyzed Decarboxylation of Aromatic Carboxylic Acids

Chem Asian J. 2023 Sep 1;18(17):e202300533. doi: 10.1002/asia.202300533. Epub 2023 Jul 27.

Authors

Reina Nonami¹, Yu Kishino¹, Tomokazu Yamasaki¹, Kazuya Kanemoto², Kento Iwai³, Nagatoshi Nishiwaki³, Kazutaka Shibatomi⁴, Tomohiko Shirai¹

Affiliations

¹ Department of Social Design Engineering, National Institute of Technology, Kochi College, 200-1 Monobe Otsu, Nankoku, Kochi, 783-8508, Japan.
² Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8578, Japan.
³ School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi, 782-8502, Japan.
⁴ Department of Applied Chemistry and Life Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi, Aichi, 441-8580, Japan.

PMID: 37464542
DOI: 10.1002/asia.202300533

Abstract

Practical synthetic applications of catalytic decarboxylation in producing useful molecules are limited. We report herein the cationic Ir-catalyzed decarboxylations of various electron-rich and -poor aromatic carboxylic acids to produce hydrocarbons in good yield (up to >99%). Additionally, this reaction is applicable in decarboxylative hydroarylation of bicyclic alkenes and decarboxylative fluorination, indicating the potential utility of this catalytic decarboxylation in synthetic chemistry.

Keywords: aromatic carboxylic acid; cationic iridium; decarboxylation; fluorination; hydroarylation.

Abstract

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