Electrochemical C(sp³)-H Lactonization of 2-Alkylbenzoic Acids toward Phthalides

Jee Eun Hong, Jisong Yoon, Woohyun Baek, Kyumin Kim, Jae-Hwan Kwak* and Yohan Park*

*Chungbuk National University, Heungdeok-gu, Cheongju, Chungbuk 28160; Inje University, Gimhae, Gyeongnam 50834, Republic of Korea, Email: jhkwakchungbuk.ac.kr, yohanparkinje.ac.kr

J. E. Hong, J. Yoon, W. Baek, K. Kim, J.-H. Kwak, Y. Park, Org. Lett., 2023, 25, 298-303.

DOI: 10.1021/acs.orglett.2c04211

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Abstract

An electrochemical C(sp³)-H lactonization of 2-alkylbenzoic acids provides phthalides by utilizing a graphite anode, dichloromethane as solvent, hexafluoroisopropanol as cosolvent, and n-Bu₄NClO₄ as electrolyte. This simple, intuitive, and atom-economical protocol enables the synthesis of various phthalides and other 5- and 6-membered lactones in good yields.

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Key Words

phthalides, electrochemistry

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ID: J54-Y2023