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Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization

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Abstract

A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21625203, 21871126) and the Opening Fund of KLCBTCMR, Ministry of Education (KLCBTCMR18-02).

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Authors and Affiliations

  1. Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang, 330063, China

    Ming-Bo Zhou, Yang Li, Xuan-Hui Ouyang & Jin-Heng Li

  2. Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha, 410081, China

    Ming-Bo Zhou & Jin-Heng Li

  3. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China

    Jin-Heng Li

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  1. Ming-Bo Zhou
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  2. Yang Li
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  3. Xuan-Hui Ouyang
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Correspondence to Yang Li or Jin-Heng Li.

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Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization

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Zhou, MB., Li, Y., Ouyang, XH. et al. Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization. Sci. China Chem. 63, 222–227 (2020). https://doi.org/10.1007/s11426-019-9633-x

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