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Iodine(III) reagent (ABX—N3)-induced intermolecular anti-Markovnikov hydroazidation of unactivated alkenes

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Abstract

Anti-Markovnikov hydroazidation of unactivated alkenes using ABX2014;N3 as an initiator has been developed at room temperature, wherein hydrogen azide (HN3) acts as both hydrogen and azidating agent. Notably, the HN3 reagent was generated from azidotrimethylsilane (TMSN3) and acetic acid in situ. The reaction itself displays broad substrate scope, good yields and excellent regioselectivities.

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Acknowledgements

This work was supported by the National Basic Research Program of China (973-2015CB856600), the National Natural Science Foundation of China (21532009, 21821002, 21790330, 21761142010), the Science and Technology Commission of Shanghai Municipality (17XD1404500, 17QA1405200, 17JC1401200), the strategic Priority Research Program (XDB20000000) and the Key Research Program of Frontier Science (QYZDJSSW-SLH055) of the Chinese Academy of Sciences.

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Authors and Affiliations

  1. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China

    Xiaonan Li, Pinhong Chen & Guosheng Liu

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  1. Xiaonan Li
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  2. Pinhong Chen
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  3. Guosheng Liu
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Correspondence to Guosheng Liu.

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Li, X., Chen, P. & Liu, G. Iodine(III) reagent (ABX—N3)-induced intermolecular anti-Markovnikov hydroazidation of unactivated alkenes. Sci. China Chem. 62, 1537–1541 (2019). https://doi.org/10.1007/s11426-019-9628-9

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