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Issue 23, 2020
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Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones through oxone-mediated cascade arylhydroxylation of activated alkenes

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Abstract

Hydroxyl-containing compounds are highly value-added organic molecules, and the establishment of novel methodologies for their elaboration is a long-standing challenge in organic synthesis. Here the first oxone-mediated direct arylhydroxylation of activated alkenes was developed for the synthesis of valuable hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones. The products were controlled by adjusting the structure of the starting alkenes. Moreover, the reaction was performed under simple conditions without any external additives or catalysts. Primary mechanistic studies showed that this reaction was a tandem process involving epoxidation and subsequent Friedel–Crafts alkylation, and oxone played a dual role (both the oxidant and proton source) in this process.

Graphical abstract: Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones through oxone-mediated cascade arylhydroxylation of activated alkenes

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Supplementary files

Article information


Submitted
29 Jun 2020
Accepted
21 Oct 2020
First published
21 Oct 2020

Green Chem., 2020,22, 8369-8374
Article type
Paper

Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones through oxone-mediated cascade arylhydroxylation of activated alkenes

M. Zhang, L. Liu, Q. Gou, Q. Wang, Y. Li, W. Li, F. Luo, M. Yuan, T. Chen and W. He, Green Chem., 2020, 22, 8369
DOI: 10.1039/D0GC02205E

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