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CC BY 4.0 · SynOpen 2023; 07(02): 154-160
DOI: 10.1055/s-0042-1751451
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Highly Efficient Synthesis of 3,3-Disubstituted Oxindoles through Direct Oxidative Alkylarylation of N-Arylacrylamides with Simple Alkanes

Yan Chen‡
a   Zhejiang Provincial Key Laboratory for Chemical & Biological Processing Technology of Farm Products School of Biological & Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, Zhejiang, P. R. of China
,
Weihong Song‡
b   College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 311121, P. R. of China
,
Zhixiang Zhou
a   Zhejiang Provincial Key Laboratory for Chemical & Biological Processing Technology of Farm Products School of Biological & Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, Zhejiang, P. R. of China
,
Ziye Zhang
a   Zhejiang Provincial Key Laboratory for Chemical & Biological Processing Technology of Farm Products School of Biological & Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, Zhejiang, P. R. of China
,
Kai Liu
a   Zhejiang Provincial Key Laboratory for Chemical & Biological Processing Technology of Farm Products School of Biological & Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, Zhejiang, P. R. of China
,
Xiaofei Zeng
b   College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 311121, P. R. of China
,
Xiaoyu Han  ∗
a   Zhejiang Provincial Key Laboratory for Chemical & Biological Processing Technology of Farm Products School of Biological & Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, Zhejiang, P. R. of China
› Author AffiliationsWe gratefully acknowledge the Basic Public Welfare Research Program of Zhejiang Province (LGJ22B020001) for generous financial support.
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Abstract

A direct oxidative alkylarylation reaction of N-arylacrylamides with simple alkanes for the synthesis of 3,3-disubstituted oxindoles under metal-free conditions was demonstrated. By using PhI(OAc)2 [(diacetoxy)iodobenzene] as an oxidant, a series of 3,3-disubstituted oxindoles bearing different aryl or alkyl substituents were generated in moderate to excellent chemical yields via a radical-initiated alkylation/cyclization process. The reported method features good functional group tolerance and wide substrate range, and provides an effective method for the preparation of various alkyl substituted 3,3-disubstituted oxindoles.

Key words

oxindoles - alkylarylation - N-arylacrylamide - PhI(OAc)2 - metal-free

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751451.
  • Supporting Information


Publication History

Received: 26 January 2023

Accepted after revision: 20 April 2023

Article published online:
08 May 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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