Synlett, Table of Contents Synlett 2018; 29(05): 663-667DOI: 10.1055/s-0036-1591520 letter © Georg Thieme Verlag Stuttgart · New YorkC(sp3)–H Peroxidation of 3-Substituted Indolin-2-ones under Metal-Free Conditions Wei-Wei Ying School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn , Wen-Ming Zhu School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn , Zhanghua Gao School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn , Hongze Liang School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn , Wen-Ting Wei* School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China Email: weiwenting@nbu.edu.cn› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category ◊ These authors contributed equally to this work Abstract A C(sp3)–H peroxidation of 3-substituted indolin-2-ones through radical coupling reaction has been developed under metal-free conditions. Using tert-butyl hydroperoxide both as an oxidant and as a peroxidation reagent to couple with the C(sp3)–H bonds of 3-substituted indolin-2-ones can form a new C–O bond without using any additives. This simple strategy provides a green and efficient approach to 3-peroxyindolin-2-ones in moderate to excellent yields. The resulting 3-peroxyindolin-2-ones could be further transformed into 3-hydroxyindolin-2-ones. Key words Key wordsC(sp3)–H peroxidation - metal-free - 3-substituted indolin-2-ones - tert-butyl hydroperoxide Full Text References References and Notes 1a Godula K. Sames D. Science 2006; 312: 67 1b Baran PS. Ishihara Y. Synlett 2010; 1733 1c Newhouse T. 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Then the tube was stirred at 85 °C under air for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the reaction was complete, the solution was concentrated under reduced pressure, and the mixture was purified by flash column chromatography over silica gel (hexane/ethyl acetate) to afford the desired products 3. The products were analyzed by 1H NMR and 13C NMR spectroscopy, and mass spectrometry (see Supporting Information). Typical Data for Representative Compound: 3-(tert-Butylperoxy)-3-phenylindolin-2-one (3a) White solid (0.0811 g, 91% yield). 1H NMR (400 MHz, CDCl3): δ = 8.62 (s, 1 H), 7.45–7.43 (m, 2 H), 7.34–7.25 (m, 5 H), 7.08 (t, J = 8.0 Hz, 1 H), 6.90 (d, J = 7.6 Hz, 1 H), 1.19 (s, 9 H). 13C NMR (100 MHz, CDCl3): δ= 176.3, 141.7, 136.0, 129.8, 129.0, 128.9, 128.5, 127.0, 126.5, 122.6, 110.2, 86.5, 80.9, 26.6. IR (KBr): 1678, 1113, 864 cm–1. 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