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Organocatalyzed cross-dehydrogenative coupling for C(sp3)–O bonds formation: a rapid access to α-aminoxyl isochromans

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Abstract

Tetrabutyl ammonium iodide catalyzed cross-dehydrogenative coupling reaction between α-C(sp3)–H of isochromans and N-hydroxyphathalimide has been achieved using tert-butylhydroxyperoxide as the terminal oxidant. This method offers rapid access to prevalent α-aminoxyl isochroman architectures. A diverse of synthetic isochromans was tolerated with this protocol, giving the corresponding product in moderate to good yields.

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Acknowledgements

We are grateful for financial support from the National Key R&D Program of China (Grant Number 2016YFA0202900), the National Natural Science Foundation of China (Grant Numbers 21878266, 21722609), the Fundamental Research Funds for the Central Universities (Grant Number 2018FZA4021).

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Authors and Affiliations

  1. Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Zheda Road 38, Hangzhou, 310027, China

    Yuli Zhou, Jingwen Chen, Ahmed Ali Elsayed, Zhiguo Zhang, Zongbi Bao, Qiwei Yang, Yiwen Yang & Qilong Ren

  2. Department of Photochemistry, National Research Centre, Tahrir Street, Dokki, Giza, Egypt

    Ahmed Ali Elsayed

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  1. Yuli Zhou
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  2. Jingwen Chen
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  3. Ahmed Ali Elsayed
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  4. Zhiguo Zhang
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  5. Zongbi Bao
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  6. Qiwei Yang
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  7. Yiwen Yang
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  8. Qilong Ren
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Correspondence to Zhiguo Zhang.

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Zhou, Y., Chen, J., Elsayed, A.A. et al. Organocatalyzed cross-dehydrogenative coupling for C(sp3)–O bonds formation: a rapid access to α-aminoxyl isochromans. Catal Lett 149, 574–579 (2019). https://doi.org/10.1007/s10562-018-2640-9

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  • DOI: https://doi.org/10.1007/s10562-018-2640-9

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