Electrochemical Dearomative Dicarboxylation of Heterocycles with Highly Negative Reduction Potentials

Yong You, Wataru Kanna, Hideaki Takano, Hiroki Hayashi, Satoshi Maeda* and Tsuyoshi Mita*

*Inst for Chemical Reaction Design and Discovery, Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan, Email: smaedaeis.hokudai.ac.jp, tmitaicredd.hokudai.ac.jp

Y. You, W. Kanna, H. Takano, H. Hayashi, S. Maeda, T. Mita, J. Am. Chem. Soc., 2022, 144, 3685-3695.

DOI: 10.1021/jacs.1c13032

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Abstract

An electrochemical protocol using the CO₂ radical anion produces unprecedented trans-oriented 2,3-dicarboxylic acids from N-Ac-, Boc-, and Ph-protected indoles. Further heteroaromatics with reduction potentials more positive than -3V undergo dicarboxylation, including benzofuran, benzothiophene, electron-deficient furans, thiophenes, 1,3-diphenylisobenzofuran, and N-Boc-pyrazoles.

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Key Words

indolines, electrochemistry

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ID: J48-Y2022