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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3354 - 3361

DOI: https://doi.org/10.6023/cjoc202005062

Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide

  • Lu Lingling ,
  • Li Yiming ,
  • Jiang Xuefeng
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  • a Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received date: 2020-05-23

  Revised date: 2020-06-26

  Online published: 2020-07-17

Supported by

Project supported by the National Key Research and Development Program of China (No. 2017YFD0200500), and the National Natural Science Foundation of China (Nos. 21971065, 21722202, 21672069).

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Abstract

1,2-Diiodoalkenes can be used as precursors for synthesis of functional molecules such as heterocyclic drugs and organic conjugated materials due to their derivability of functional groups. Herein, alkynes can be converted into 1,2-trans-diiodioalkenes efficiently and conveniently by using inexpensive and stable sodium iodide as iodine source and air as oxidant under the visible-light (blue light) with normal temperature and atmospheric pressure. The corresponding reactions were operated under mild conditions with inexpensive and easily accessible reagents, which obviate the need of transition-metal-catalysts or oxidizing reagents. Meanwhile, this method is compatible with a wide range of substrates, including terminal and internal alkynes even the peptide and carbohydrates containing a variety of heteroatoms and active hydrogen.

Key words： 1,2-diiodoalkenes; alkynes; diiodination; visible-light

Cite this article

Lu Lingling , Li Yiming , Jiang Xuefeng . Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3354 -3361 . DOI: 10.6023/cjoc202005062

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