Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3354-3361.DOI: 10.6023/cjoc202005062 Previous Articles     Next Articles

Special Issue: 有机光催化虚拟合辑 黄乃正院士七十华诞专辑


鲁玲玲a, 李一鸣a, 姜雪峰a,b   

  1. a 华东师范大学化学与分子工程学院 上海市绿色化学与化工过程绿色化重点实验室 上海 200062;
    b 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2020-05-23 修回日期:2020-06-26 发布日期:2020-07-17
  • 通讯作者: 姜雪峰
  • 基金资助:

Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide

Lu Linglinga, Li Yiminga, Jiang Xuefenga,b   

  1. 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:2020-05-23 Revised:2020-06-26 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).

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