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Visible-light-induced regioselective cross-dehydrogenative coupling of 2-isothiocyanatonaphthalenes with amines using molecular oxygen

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Abstract

An efficient and eco-friendly protocol for the construction of naphtho[2,1-d]thiazol-2-amines through visible-light photoredoxcatalyzed C(sp2)-H/S-H cross-dehydrogenative coupling reactions between 2-isothiocyanatonaphthalenes and amines was established. In this reaction, the new C-N and C-S bonds are formed simultaneously in a single step. This new method provides a straightforward approach for constructing valuable sulfur-containing compounds.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21302110, 21702119), the Natural Science Foundation of Shandong Province (ZR2016JL012, ZR2017QB001), the Scientific Research Foundation of Qingdao University of Science and Technology, the Natural Science Foundation of Liaoning Province (20180550882) and the Program for Creative Talents in University of Liaoning Province.

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Authors and Affiliations

  1. Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, Ministry of Education, Shandong Key Laboratory of Biochemical Analysis; College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Ziyu Gan, Qiuli Yan, Guiyun Xu & Daoshan Yang

  2. School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, 273165, China

    Ziyu Gan, Guoqing Li, Yuan-Ye Jiang & Daoshan Yang

  3. Institute of Catalysis for Energy and Environment, College of Chemistry & Chemical Engineering, Shenyang Normal University, Shenyang, 110034, China

    Xiaobo Yang

  4. Qingdao West Coast New Area Poli Junior Middle School, Qingdao, 266409, China

    Gaoyang Li

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  1. Ziyu Gan
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  2. Guoqing Li
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  3. Xiaobo Yang
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  4. Qiuli Yan
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  5. Guiyun Xu
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  6. Gaoyang Li
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  7. Yuan-Ye Jiang
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Correspondence to Yuan-Ye Jiang or Daoshan Yang.

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The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Gan, Z., Li, G., Yang, X. et al. Visible-light-induced regioselective cross-dehydrogenative coupling of 2-isothiocyanatonaphthalenes with amines using molecular oxygen. Sci. China Chem. 63, 1652–1658 (2020). https://doi.org/10.1007/s11426-020-9811-6

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