FeIII/TBHP mediated remote C–O bond construction of 8-aminoquinolines: access to methoxylation and cyanomethoxylation

Mengfei Zhao; Kaixin Zhang; Jianxiong Xu; Jizhen Li

doi:10.1039/D2QO00438K

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Fe^III/TBHP mediated remote C–O bond construction of 8-aminoquinolines: access to methoxylation and cyanomethoxylation†

Mengfei Zhao,^a Kaixin Zhang,^a Jianxiong Xu^a and Jizhen Li

*^ab

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, College of Chemistry, Jilin University, 2519 Jiefang Road, Changchun 130021, P. R. China
E-mail: ljz@jlu.edu.cn

^b State Key laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, P.R. China

Abstract

Novel approaches to C5 selective methoxylation and cyanomethoxylation of 8-aminoquinolines under the Fe^III/TBHP system were developed. Various substituted quinolines were tolerated to afford the corresponding ether products. A plausible mechanism was proposed involving the addition of alkoxyl radicals to an iron-chelated intermediate. In these protocols, TBHP acted as not only a radical initiator, more importantly, but also an “oxygen” source involved in the ether bond formation, which was investigated successfully for the first time.

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Article information

DOI: https://doi.org/10.1039/D2QO00438K
Article type: Research Article
Submitted: 18 Mar 2022
Accepted: 13 Jun 2022
First published: 16 Jun 2022

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Org. Chem. Front., 2022,9, 4063-4069

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Fe^III/TBHP mediated remote C–O bond construction of 8-aminoquinolines: access to methoxylation and cyanomethoxylation

M. Zhao, K. Zhang, J. Xu and J. Li, Org. Chem. Front., 2022, 9, 4063 DOI: 10.1039/D2QO00438K

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