HAT-Mediated Electrochemical C(sp²)-H Acylation of Quinolines with Alcohols

Yujie Liao, Cong Jiang, Congcong Qiang, Ping Liu* and Peipei Sun*

*School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023, China, Email: pingliunjnu.edu.cn, sunpeipeinjnu.edu.cn

Y. Liao, C. Jiang, C. Qiang, P. Liu, P. Sun, Org. Lett., 2023, 25, 7327-7331.

DOI: 10.1021/acs.orglett.3c02668

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Abstract

An electrochemical hydrogen atom transfer (HAT) strategy enables a C(sp²)-H formylation of electron-deficient quinolines and isoquinolines using methanol as a formyl source with a catalytic amount of N-hydroxyphthalimide (NHPI) as hydrogen atom transfer (HAT) catalyst. This transition-metal and oxidant-free method could also be applied to the direct C(sp²)-H acetylation or propionylation.

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proposed mechanism

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Key Words

quinolines, formylation, electrochemistry

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ID: J54-Y2023