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

Yujie Liao; Cong Jiang; Congcong Qiang; Ping Liu; Peipei Sun

doi:10.1021/acs.orglett.3c02668

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

Org Lett. 2023 Oct 13;25(40):7327-7331. doi: 10.1021/acs.orglett.3c02668. Epub 2023 Oct 5.

Authors

Yujie Liao¹, Cong Jiang¹, Congcong Qiang¹, Ping Liu¹, Peipei Sun¹

Affiliation

¹ School of Chemistry and Materials Science, Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing Normal University, Nanjing 210023, China.

PMID: 37795817
DOI: 10.1021/acs.orglett.3c02668

Abstract

Herein, an electrochemical hydrogen atom transfer (HAT) strategy for C(sp²)-H formylation of electron-deficient quinolines and isoquinolines is described. The cheap methanol acts as a formyl source with a catalytic amount of N-hydroxyphthalimide (NHPI) as the hydrogen atom transfer (HAT) catalyst. The advantages of this reaction are transition-metal-catalyst- and chemical-oxidant-free conditions, and the protocol could also be applied to the direct C(sp²)-H acetylation or propionylation of quinolines.