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Synthesis 2018; 50(23): 4645-4650
DOI: 10.1055/s-0037-1610537
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Selective Synthesis of 3-Hydroxy-2-oxindoles via Cascade C–H Cycloaddition and Oxidation of α-Aminoaceto­phenones

Yan-Yan Liao
Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn   Email: wzheng@scau.edu.cn
,
Li Xu
Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn   Email: wzheng@scau.edu.cn
,
Ri-Yuan Tang*
Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn   Email: wzheng@scau.edu.cn
,
Wen-Xu Zheng*
Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn   Email: wzheng@scau.edu.cn
› Author AffiliationsWe gratefully acknowledge the financial support of South China Agricultural University and the Science Technology Program Project of Guangdong Province (No. 2016B020204005).
Further Information

Publication History

Received: 18 May 2018

Accepted after revision: 06 July 2018

Publication Date:
08 August 2018 (online)

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Abstract

A novel method for the synthesis of 3-hydroxy-2-oxindole (3-hydroxyindolin-2-one) derivatives by palladium-catalyzed tandem C–H cycloaddition and oxidation of α-aminoacetophenone has been developed. In the presence of Pd(OAc)2 and AgOAc, a variety of 3-hydroxy-2-oxindoles were synthesized in moderate yields. Control experiments show that the selective cycloaddition occurs prior to the oxidation is crucial for this successful chemical transformation.

Key words

palladium - indole - cyclization - oxidation - C–H functionalization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610537.
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