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Dinuclear gold-catalyzed C-H bond functionalization of cyclopropenes

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Abstract

We report an unprecedented C–H bond functionalization of cyclopropenes enabled by dinuclear gold catalysis. Highly selective C–H allylation, alkynylation and halogenation of cyclopropenes with organic halides have been realized. The reaction does not require strong external oxidants and affords access to functionalized cyclopropenes in moderate to good yields. The reductive elimination process to controllably construct C–C or C–X bonds can be tuned by using different dinuclear gold catalysts.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22001116, 22001117, 21971111, 21971108, 21732003), the Natural Science Foundation of Jiangsu Province (BK20190006, BK20190285), the Fundamental Research Funds for the Central Universities (020514380252), the “Innovation & Entrepreneurship Talents Plan” of Jiangsu Province, the Guangdong Basic and Applied Basic Research Foundation (2020A1515110816) and the Foundation of Advanced Catalytic Engineering Research Center of the Ministry of Education of Hunan University. Xiaopeng Wu, Dongping Wang and Wenliang Wang are warmly acknowledged for reproducing experimental procedures for products 4a, 5h and 6d.

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Authors and Affiliations

  1. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China

    Kai Liu, Tingrui Li, Duan-Yang Liu, Weipeng Li, Jian Han, Chengjian Zhu & Jin Xie

  2. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China

    Kai Liu

  3. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, 450001, China

    Chengjian Zhu

  4. Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, 410082, China

    Jin Xie

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  1. Kai Liu
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  2. Tingrui Li
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  3. Duan-Yang Liu
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Correspondence to Jin Xie.

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Liu, K., Li, T., Liu, DY. et al. Dinuclear gold-catalyzed C-H bond functionalization of cyclopropenes. Sci. China Chem. 64, 1958–1963 (2021). https://doi.org/10.1007/s11426-021-1031-x

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