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Synlett 2019; 30(01): 109-113
DOI: 10.1055/s-0037-1610672
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed C(sp3)–H Azidation of 1,3-Dihydro-2H-indol-2-ones Under Mild Conditions

Wen-Hui Bao
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Le-Han Gao
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Wei-Wei Ying
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Wei-Ting Chen
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Gan-Ping Chen
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Wen-Ting Wei*
a   School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Yan-Yun Liu*
b   Department of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China
,
Qiang Li
c   Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, P. R. of China
› Author AffiliationsThis research is sponsored by the National Natural Science Foundation of China (Grant 21801142), the Natural Science Foundation of Zhejiang Province (No. LQ18B020002), State Key Laboratory of Analytical Chemistry for Life Science (No. SKLACLS1804), the Open Subject of State Key Laboratory of Chemo/Biosensing and Chemometrics (2017016), Education Foundation of Zhejiang Province (No. Y201737123), and the K. C. Wong Magna Fund in Ningbo University.
Further Information

Publication History

Received: 15 August 2018

Accepted after revision: 16 October 2018

Publication Date:
14 November 2018 (online)

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◊These authors contributed equally to this work.

Abstract

A simple and economical synthesis of 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones has been realized under mild conditions through copper-catalyzed C(sp3)–H azidation of the corresponding 1,3-dihydro-2H-indol-2-ones with trimethylsilyl azide. The reaction proceeds by an efficient pathway involving the addition of a N3 radical to the enol tautomer and consecutive C(sp3)−N bond formations. The method is valuable because of its mild reaction conditions, short reaction times, and broad substrate scope, and because of the rich biological activity of the resulting 3-substituted 3-azido-1,3-dihydro-2H-indol-2-one products.

Keywords

copper catalysis - radical reaction - azidoindolinones - indolinones - azidation - trimethylsilyl azide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-00360037-1610672.
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