Citation: 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 shu

Visible-Light-Promoted Diiodination of Alkynes Using Sodium Iodide

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

Corresponding author: Jiang Xuefeng, xfjiang@chem.ecnu.edu.cn
Received Date: 23 May 2020
Revised Date: 26 June 2020
Available Online: 15 July 2020
Fund Project: the National Natural Science Foundation of China 21722202Project 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)the National Natural Science Foundation of China 21971065the National Natural Science Foundation of China 21672069the National Key Research and Development Program of China 2017YFD0200500

Figures(2)

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.
- 1, 2-diiodoalkenes,
- alkynes,
- diiodination,
- visible-light
1. [1]
  (a) Seechurn, C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
  (b) Piontek, A.; Bisz, E.; Szostak, M. Angew. Chem., Int. Ed. 2018, 57, 11116.
  (c) King, A. O.; Yasuda, N. In Organometallics in Process Chemistry, Springer, Berlin, 2004, pp. 205~245.
  (d) Ian, W. Ph.D. Dissertation, Durham University, Durham, 2011.
  (e) Zeng, X.; Liu, S.; Yang, Y.; Yang, Yi; Hammond, G. B.; Xu, B. Chem 2020, 6, 1018.
2. [2]
  (a) Zani, L.; Dessì, A.; Franchi, D.; Calamante, M.; Reginato, G.; Mordini, A. Coord. Chem. Rev. 2019, 392, 177.
  (b) Kawabata, K.; Saito, M.; Osaka, I.; Takimiya, K. J. Am. Chem. Soc. 2016, 138, 7725.
  (c) Furukawa, S.; Yasuda, T. J. Mater. Chem. A 2019, 7, 14806.
  (d) Chen, L.; Zeng, M.; Weng, C.; Tan, S.; Shen, P. ACS Appl. Mater. Interfaces 2019, 11, 48134.
  (e) Tovar, J. D. Synthesis 2011, 2387.
  (f) Olla, T.; Ibraikulov, O. A.; Ferry, S.; Boyron, O.; Méry, S.; Heinrich, B.; Heiser, T.; Lévêque, P.; Leclerc, N. Macromolecules 2019, 52, 8006.
3. [3]
  (a) Atzrodt, J.; Derdau, V.; Fey, T.; Zimmermann, J. Angew. Chem., Int. Ed. 2007, 46, 7744.
  (b) Liu, C.; Chen, Z.; Su, C.; Zhao, X.; Gao, Q.; Ning, G.-H.; Zhu, H.; Tang, W.; Leng, K.; Fu, W.; Tian, B.; Peng, X.; Li, J.; Xu, Q.-H.; Zhou, W.; Loh, K. P. Nat. Commun. 2018, 9, 80.
4. [4]
  (a) Welch, M. J.; Redvanly, C. S. In The Hand Book of Radiopharmaceuticals: Radiochemistry and Applications, Ed.: Finn, R., Wiley, New York, 2003, p. 423.
  (b) Hallouard, F.; Anton, N.; Choquet, P.; Constantinesco, A.; Vandamme, T. Biomaterials 2010, 31, 6249.
  (c) Zimprich, F.; Rath, J.; Mauritz, M.; Zulehner, G.; Hilfer, Eva.; Cetin, H.; Kasprian, G.; Auff, E. J. Neurol. 2017, 264, 1209.
5. [5]
  (a) Gkotsi, D. S.; Ludewig, H.; Sharma, S. V.; Connolly, J. A.; Dhaliwal, J.; Wang, Y.; Unsworth, W. P.; Taylor, R. J. K.; McLachlan, M. M. W.; Shanahan, S.; Naismith, J. H.; Goss, R. J. M. Nat. Chem. 2019, 11, 1091.
  (b) Butler, A.; Sandy, M. Nature 2009, 460, 848.
  (c) Latham, J.; Brandenburger, E.; Shepherd, A.; Menon, B. R. K.; Micklefield, J. Chem. Rev. 2018, 118, 232.
6. [6]
  Li, Y.; Mou, T.; Lu, L.; Jiang, X. Chem. Commun., 2019, 55, 14299. doi: 10.1039/C9CC07655G
7. [7]
  (a) Banerjee, S.; Khatri, H.; Balasanthiran, V.; Koodali, R. T.; Sereda, G. Tetrahedron 2011, 67, 5717.
  (b) Ranu, B. C.; Adak, L.; Chattopadhyay, K. J. Org. Chem. 2008, 73, 5609.
  (c) Kimura, T.; Nishimura, Y.; Ishida, N.; Momochi, H.; Yamashita, H.; Satoh, T. Tetrahedron Lett. 2013, 54, 1049.
8. [8]
  (a) Bao, Y.; Yang, X.; Zhou, Q.; Yang, F. Org. Lett. 2018, 20, 1966.
  (b) Lin, Y.; Lu, G.; Cai, C.; Yi, W. Org. Lett. 2015, 17, 3310.
9. [9]
  Li, J. H.; Tang, S. Synth. Commun. 2005, 35, 105. doi: 10.1081/SCC-200046514
10. [10]
  (a) Liang, Y.; Tao, L.-M.; Zhang, Y.-H.; Li, J.-H. Synthesis 2008, 3988.
  (b) Raff, G.; Belot, S.; Balme, G.; Monteiro, N. Org. Biomol. Chem. 2011, 9, 1474.
11. [11]
  Schuh, K.; Glorius, F. Synthesis 2007, 2297.
12. [12]
  Shen, G.; Yang, B.; Huang, X.; Hou, Y.; Gao, H.; Cui, J.; Cui, C.; Zhang, T. J. Org. Chem. 2017, 82, 3798. doi: 10.1021/acs.joc.7b00162
13. [13]
  Woodward, S.; Ackermann, M.; Ahirwar, S. K.; Burroughs, L.; Garrett, M. R.; Ritchie, J.; Shine, J.; Tyril, B.; Simpson, K.; Woodward, P. Chem. Eur. J. 2017, 3, 7819.
14. [14]
  (a) Sun, A.; Lauher, J. W.; Goroff, N. S. Science 2006, 312, 1030.
  (b) DeCicco, R. C.; Luo, L.; Goroff, N. S. Acc. Chem. Res. 2019, 52, 2080.
15. [15]
  Terent'ev, A. O.; Borisov, D. A.; Krylov, I. B.; Nikishin, G. I. Synth. Commun. 2007, 37, 3151. doi: 10.1080/00397910701545171
16. [16]
  (a) Dolbier, W. R.; Duan, J.-X.; Chen, Q.-Y. J. Org. Chem. 1998, 63, 9486.
  (b) Li, J.-H.; Tang, S. Synth. Commun. 2005, 35, 105.
  (c) Su, L.; Lei, C.-Y.; Fan, W.-Y.; Liu, L.-X. Synth. Commun. 2011, 41, 1200.
17. [17]
  (a) Li, J.-H.; Xie, Y.-X.; Yin, D.-L. Green Chem. 2002, 4, 505.
  (b) Larson, S.; Luidhardt, T.; Kabalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1988, 29, 35.
  (c) Song, S.; Li, X.; Wei, J.; Wang, W.; Zhang, Y.; Ai, L.; Zhu, Y.; Shi, X.; Zhang, X.; Jiao, N. Nat. Catal. 2020, 3, 107.
18. [18]
  Banothu, R.; Peraka, S.; Kodumuri, S.; Chevella, D.; Gajula, K. S.; Amrutham, V.; Yennamaneni, D. R.; Nama, N. New J. Chem. 2018, 42, 17879. doi: 10.1039/C8NJ03929A
19. [19]
  Stavber, S.; Stavber, G.; Iskra, J.; Zupan, M. Adv. Synth. Catal. 2008, 350, 2921. doi: 10.1002/adsc.200800553
20. [20]
  Guo, C.-C.; Jiang, Q.; Wang, J.-Y. Synthesis 2015, 47, 2081. doi: 10.1055/s-0034-1379910
21. [21]
  (a) Liu, Y.; Maruoka, K.; Huang, D.-Y.; Huang, J. J. Org. Chem. 2017, 82, 11865.
  (b) Kashyap, S.; Rao D. S.; Reddy, T. R. Org. Biomol. Chem. 2018, 16, 1508.
22. [22]
  Madabhushi, S.; Jillella, R.; Mallu, K. K. R.; Golada, K. R.; Vangipuram, V. S. Tetrahedron Lett. 2013, 54, 3993. doi: 10.1016/j.tetlet.2013.05.072
23. [23]
  Yang, F.; Jin, T.; Bao, M.; Yamamoto, Y. Chem. Commun. 2011, 47, 4013. doi: 10.1039/c0cc05442a
1. [1]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
2. [2]
  Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO₄/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212
3. [3]
  Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd_0.5Zn_0.5S Nanorods on Ti₃C₂ MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-. doi: 10.3866/PKU.WHXB202402016
4. [4]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
5. [5]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
6. [6]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
7. [7]
  Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
8. [8]
  Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
9. [9]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
10. [10]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
11. [11]
  Xiting Zhou , Zhipeng Han , Xinlei Zhang , Shixuan Zhu , Cheng Che , Liang Xu , Zhenyu Sun , Leiduan Hao , Zhiyu Yang . Dual Modulation via Ag-Doped CuO Catalyst and Iodide-Containing Electrolyte for Enhanced Electrocatalytic CO₂ Reduction to Multi-Carbon Products: A Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(7): 336-344. doi: 10.12461/PKU.DXHX202412070
12. [12]
  Hongmei Chai , Yixia Ren , Xiangyang Hou , Long Tang , Jiawei Xie . 智能手机光传感的“丙酮碘化反应”实验改进. University Chemistry, 2025, 40(6): 193-200. doi: 10.12461/PKU.DXHX202407086
13. [13]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
14. [14]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
15. [15]
  Qilin YU , Yifei XU , Pengjun ZHANG , Shuwei HAO , Chongqiang ZHU , Chunhui YANG . Effect of regulating K⁺/Na⁺ ratio on the structure and optical properties of double perovskite Cs₂NaBiCl₆: Mn²⁺. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1058-1067. doi: 10.11862/CJIC.20240418
16. [16]
  Xuzhen Wang , Xinkui Wang , Dongxu Tian , Wei Liu . Enhancing the Comprehensive Quality and Innovation Abilities of Graduate Students through a “Student-Centered, Dual Integration and Dual Drive” Teaching Model: A Case Study in the Course of Chemical Reaction Kinetics. University Chemistry, 2024, 39(6): 160-165. doi: 10.3866/PKU.DXHX202401074
17. [17]
  Lei Shu , Zhengqing Hao , Kai Yan , Hong Wang , Lihua Zhu , Fang Chen , Nan Wang . Development of a Double-Carbon Related Experiment: Preparation, Characterization and Carbon-Capture Ability of Eggshell-Derived CaO. University Chemistry, 2024, 39(4): 149-156. doi: 10.3866/PKU.DXHX202310134
18. [18]
  Jin Yan , Chengxia Tong , Yajie Li , Yue Gu , Xuejian Qu , Shigang Wei , Wanchun Zhu , Yupeng Guo . Construction of a “Dual Support, Triple Integration” Chemical Safety Practical Education System. University Chemistry, 2024, 39(7): 69-75. doi: 10.12461/PKU.DXHX202405008
19. [19]
  Linhan Tian , Changsheng Lu . Discussion on Sextuple Bonding in Diatomic Motifs of Chromium Family Elements. University Chemistry, 2024, 39(8): 395-402. doi: 10.3866/PKU.DXHX202401056
20. [20]
  Wei Gao , Jinyue Yang , Wenwei Zhang . Practice and Exploration of Promoting the “Double Reduction” Work with Popular Science Resources in Universities. University Chemistry, 2024, 39(9): 385-391. doi: 10.3866/PKU.DXHX202311008

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1458)
HTML views(146)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142