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

Wen-Hui Bao; Le-Han Gao; Wei-Wei Ying; Wei-Ting Chen; Gan-Ping Chen; Wen-Ting Wei; Yan-Yun Liu; Qiang Li

doi:10.1055/s-0037-1610672

Synlett, Table of Contents

Synlett 2019; 30(01): 109-113
DOI: 10.1055/s-0037-1610672

letter

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

Wen-Hui Bao

^aSchool of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn

,

Le-Han Gao

^aSchool of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn

,

Wei-Wei Ying

^aSchool of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn

,

Wei-Ting Chen

^aSchool of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn

,

Gan-Ping Chen

^aSchool of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn

,

Wen-Ting Wei*

^aSchool of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn

,

Yan-Yun Liu*

^bDepartment of Chemistry and Materials Engineering, Huaihua University, Huaihua 418008, P. R. of China

,

Qiang Li

^cInstitution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, P. R. of China

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Abstract

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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

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