Issue 43, 2019

Transition-metal- and oxidant-free three-component reaction of quinoline N-oxides, sodium metabisulfite and aryldiazonium tetrafluoroborates via a dual radical coupling process

Abstract

A convenient and straightforward three-component transformation of quinoline N-oxides, sodium metabisulfite and aryldiazonium tetrafluoroborates has been developed, providing the target products in moderate to good yields. Compared with previous studies, the present methodology avoids the use of transition-metal catalysts and excess oxidants, providing a simple and practical alternative approach for the construction of 2-sulfonylquinolines. Control experiments indicate that a dual radical coupling process is responsible for this reaction.

Graphical abstract: Transition-metal- and oxidant-free three-component reaction of quinoline N-oxides, sodium metabisulfite and aryldiazonium tetrafluoroborates via a dual radical coupling process

Supplementary files

Article information

Article type
Paper
Submitted
28 Sep 2019
Accepted
17 Oct 2019
First published
21 Oct 2019

Org. Biomol. Chem., 2019,17, 9479-9488

Transition-metal- and oxidant-free three-component reaction of quinoline N-oxides, sodium metabisulfite and aryldiazonium tetrafluoroborates via a dual radical coupling process

G. You, D. Xi, J. Sun, L. Hao and C. Xia, Org. Biomol. Chem., 2019, 17, 9479 DOI: 10.1039/C9OB02106J

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