Issue 48, 2022
From the journal:

Organic & Biomolecular Chemistry

Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane†

Yi-Na Li,‡a   Ming-Xi Zhou,‡a   Jin-Bo Wu,a   Zhen Wang ORCID logo *a  and  Yao-Fu Zeng ORCID logo *a  

* Corresponding authors

a School of Pharmaceutical Science, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Hengyang Medical School, University of South China, Hengyang, Hunan, China
E-mail: zhenw@lzu.edu.cn, zengyf@usc.edu.cn

Abstract

A metal-free tandem reduction and N-trifluoroethylation of quinolines and quinoxalines has been developed. It provided a convenient route to access trifluoroethylated tetrahydroquinolines and tetrahydroquinoxalines. This one-pot method avoids the purification process of the intermediate. Mechanistically, the in situ-generated boryl acetal species reacted with tetrahydroquinolines to generate iminiums followed by reduction to give the target compounds.

Graphical abstract: Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane

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Article information

DOI
https://doi.org/10.1039/D2OB01923J
Article type
Communication
Submitted
20 Oct 2022
Accepted
16 Nov 2022
First published
24 Nov 2022

Org. Biomol. Chem., 2022,20, 9613-9617

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Tandem reduction and trifluoroethylation of quinolines and quinoxalines with trifluoroacetic acid and trimethylamine borane

Y. Li, M. Zhou, J. Wu, Z. Wang and Y. Zeng, Org. Biomol. Chem., 2022, 20, 9613 DOI: 10.1039/D2OB01923J

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