Direct C(sp3)–H acyloxylation of indolin-3-ones with carboxylic acids catalysed by KI

Yong-Long Zhao; Yong-Qin Tang; Xing-Hai Fei; Fen-Fen Yang; Zhuo-Xian Cao; Dong-Zhu Duan; Qing-Jie Zhao; Yuan-Yong Yang; Meng Zhou; Bin He

doi:10.1039/C9GC04446A

Direct C(sp³)–H acyloxylation of indolin-3-ones with carboxylic acids catalysed by KI†

Yong-Long Zhao,

‡*^a Yong-Qin Tang,‡^a Xing-Hai Fei,^a Fen-Fen Yang,^a Zhuo-Xian Cao,^a Dong-Zhu Duan,^b Qing-Jie Zhao,^c Yuan-Yong Yang,^a Meng Zhou^a and Bin He*^a

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* Corresponding authors

^a State Key Laboratory of Functions and Applications of Medicinal Plants, Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), and School of Pharmacy, Guizhou Medical University, Guiyang 550004, P.R. China
E-mail: zhaoyl05@126.com, zhaoyonglong@gmc.edu.cn

^b Shaanxi Key Laboratory of Phytochemistry, Baoji University of Arts and Sciences, Baoji 721013, P.R. China

^c Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. China

Abstract

The first KI-catalyzed direct acyloxylation of indolin-3-ones with carboxylic acids has been developed using 30% aq. H₂O₂ as a green oxidant at room temperature. Through this strategy, various C2-acyloxy indolin-3-ones were obtained in up to 96% yield. Moreover, the C2-acyloxy indolin-3-ones can serve as versatile intermediates for the synthesis of nucleophilic 2-monoarylated indolin-3-ones and 3-ylidene indoles.

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Direct C(sp³)–H acyloxylation of indolin-3-ones with carboxylic acids catalysed by KI†

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Direct C(sp³)–H acyloxylation of indolin-3-ones with carboxylic acids catalysed by KI

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