Citation: Zhang Nannan, Zuo Hangdong, Xu Chen, Pan Junyi, Sun Jun, Guo Cheng. Visible light induced the high-efficiency spirocyclization reaction of propynamide and thiophenols via recyclable catalyst Pd/ZrO₂[J]. Chinese Chemical Letters, ;2020, 31(2): 337-340. doi: 10.1016/j.cclet.2019.06.008 shu

Visible light induced the high-efficiency spirocyclization reaction of propynamide and thiophenols via recyclable catalyst Pd/ZrO₂

College of Chemistry and molecular engineering, Nanjing Tech University, Nanjing 211816 China

sunjun@njtech.edu.cn

guocheng@njtech.edu.cn

Received Date: 24 April 2019
Revised Date: 30 May 2019
Accepted Date: 5 June 2019
Available Online: 6 June 2019

Figures(6)

A new method for the synthesis of 3-thioazaspiro[4,5]trienones was developed using Pd nanoparticle catalysts, which are highly efficient, environmentally friendly and recyclable. Alkynes and thiophene phenols are effectively cyclized by Pd/ZrO₂ catalyst under visible light irradiation. The present protocol simply utilizes visible light as the safe and ecofriendly energy source, and the Pd/ZrO₂ nanocomposite as photocatalyst provides a simple and practical approach to various 3-thioazaspiro[4,5]trienones in moderate conditions to high yields
- Visible light,
- Spirocyclization reaction,
- Mild condition,
- Pd/ZrO₂ nanocomposite photocatalyst
1. [1]
  J. Kobayashi, T. Kubota, Nat. Prod. Rep. 26(2009) 936-962. doi: 10.1039/b813006j
2. [2]
  H.B. Park, Y.J. Kim, J.K. Lee, K.R. Lee, H.C. Kwon, Org. Lett.14(2012) 5002-5005. doi: 10.1021/ol302115z
3. [3]
  Y.L. Yang, F.R. Chang, Y.C. Wu, Helv. Chim. Acta 87(2004) 1392-1399. doi: 10.1002/hlca.200490127
4. [4]
  V.A. D'yakonov, O.A. Trapeznikova, A.D. Meijere, U.M. Dzhemilev, Chem. Rev. 114(2014) 5775-5814. doi: 10.1021/cr400291c
5. [5]
  W.T. Wu, L. Zhang, S.L. You, Chem. Soc. Rev. 45(2016) 1570-1580. doi: 10.1039/C5CS00356C
6. [6]
  W.H. Bao, C. Wu, W.M. He, Org. Biomol. Chem. 16(2018) 8403-8407. doi: 10.1039/C8OB01820K
7. [7]
  L.Y. Xie, Y.J. Li, W.M. He, Green Chem. 19(2017) 5642-5646. doi: 10.1039/C7GC02304A
8. [8]
  Q.S. Liu, W. Wei, Green Chem. 21(2019) 1609-1613. doi: 10.1039/C9GC00222G
9. [9]
  W. Wei, H. Cui, D. Yang, H. Wang, Green Chem. 19(2017) 5608-5613. doi: 10.1039/C7GC02330H
10. [10]
  H. Cui, W. Wei, D. Yang, H. Wang, RSC Adv. 5(2015) 84657-84661. doi: 10.1039/C5RA16548B
11. [11]
  X.H. Yang, R.J. Song, Y. Li, B. Liu, J. Org. Chem. 79(2014) 4582-4589. doi: 10.1021/jo5005982
12. [12]
  W.T. Wang, J.H. Li, Org. Chem. Front. 1(2014) 484-489. doi: 10.1039/c4qo00006d
13. [13]
  L.J. Wang, A.Q. Wang, Y. Xia, X.X. Wu, X.Y. Liu, Chem. Commun. 50(2014) 13998-14001. doi: 10.1039/C4CC06923D
14. [14]
  L. Wu, F.L. Tan, M. Li, Org. Chem. Front. 4(2017) 350-353. doi: 10.1039/C6QO00691D
15. [15]
  Y.Q. Yuan, P.S. Kumar, C.N. Zhang, M.H. Yang, S.R. Guo, Org. Biomol. Chem. 15(2017) 7330-7338. doi: 10.1039/C7OB01552F
16. [16]
  X. Yang, X. Ouyang, W. Wei, J. Li, Adv. Syn. Catal. 46(2015) 1161-1166.
17. [17]
  T. Tana, X.W. Guo, Chem. Commun. 52(2016) 11567-11570. doi: 10.1039/C6CC05186C
18. [18]
  Q. Xiao, E. Jaatinen, H. Zhu, Chem. Asian J. 9(2014) 3046-3064. doi: 10.1002/asia.201402310
19. [19]
  D.P. Hari, B. Konig, Angew. Chem. Int. Ed. 52(2013) 4734-4743. doi: 10.1002/anie.201210276
20. [20]
  S. Ni, J. Cao, H. Mei, Y. Pan, Green Chem. 18(2016) 3935-3939. doi: 10.1039/C6GC01027J
21. [21]
  S. Sarina, H. Zhu, E. Jaatinen, et al., J. Am. Chem. Soc. 135(2013) 5793-5801. doi: 10.1021/ja400527a
22. [22]
  M. Hartings, Nature Chem. 4(2012) 764. doi: 10.1038/nchem.1437
23. [23]
  S.S. Stahl, Science 309(2005) 1824-1826. doi: 10.1126/science.1114666
24. [24]
  C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 51(2012) 5062-5085. doi: 10.1002/anie.201107017
25. [25]
  T.Y. Shang, L.H. Lu, Z. Cao, et al., Chem. Commun. 55(2019) 5408-5419. doi: 10.1039/C9CC01047E
26. [26]
  B.H. Zhang, C.Y. He, Chin. Chem. Lett. 28(2017) 1751-1754. doi: 10.1016/j.cclet.2017.03.039
27. [27]
  D.Q. Dong, Z.L. Wang, Chin. Chem. Lett. 28(2017) 1597-1599. doi: 10.1016/j.cclet.2017.03.008
28. [28]
  R.Z. Mao, X.S. Ye, Chin. Chem. Lett. 29(2017) 61-64.
29. [29]
  Y.Q. Ge, P.H. Diao, C. Guo, Chin. Chem. Lett. 29(2018) 903-906. doi: 10.1016/j.cclet.2018.01.002
30. [30]
  L.H. Wang, X.L. Cui, Chin. Chem. Lett. 29(2018) 907-910. doi: 10.1016/j.cclet.2018.05.007
31. [31]
  W. Wei, C. Liu, D. Yang, et al., Chem. Commun. 49(2013) 10239-10241. doi: 10.1039/c3cc45803b
32. [32]
  Q. Xiao, S. Sarina, H. Zhu, ACS Catal. 4(2014) 1725-1734. doi: 10.1021/cs5000284
33. [33]
  Q. Xiao, S. Sarina, J. Esa, H. Zhu, Green Chem. 16(2014) 4272-4285. doi: 10.1039/C4GC00588K
34. [34]
  Q. Xiao, Z. Liu, A. Bo, et al., J. Am. Chem. Soc. 137(2015) 1956-1966. doi: 10.1021/ja511619c
35. [35]
  S. Sarina, S. Bai, H. Zhu, Green Chem. 16(2014) 331-341. doi: 10.1039/C3GC41866A
36. [36]
  J. Zhao, Z. Zheng, S. Bottle, et al., Chem. Commun. 49(2013) 2676-2678. doi: 10.1039/c3cc38985e
37. [37]
  W. Cui, Q. Xiao, S. Sarina, Catal. Today 235(2014) 152-159. doi: 10.1016/j.cattod.2014.04.015
38. [38]
  Z. Xing, M. Yang, H. Sun, Green Chem. 20(2018) 5117-5122. doi: 10.1039/C8GC02237B
39. [39]
  H.F. Qian, C.K. Li, J.P. Zou, Org. Lett. 20(2018) 5947-5951. doi: 10.1021/acs.orglett.8b02639
40. [40]
  Y. Zhang, L. Pei, Z.J. Zheng, Mater. Chem. A 3(2015) 18045-18052. doi: 10.1039/C5TA03214H
1. [1]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
2. [2]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
3. [3]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
4. [4]
  Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
5. [5]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
6. [6]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
7. [7]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
8. [8]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
9. [9]
  Xin Wang , Changzhao Chen , Qishen Wang , Kai Dai . Graphene quantum dot modified Bi2MoO6 nanoflower for efficient degradation of BPA under visible light. Chinese Journal of Structural Chemistry, 2024, 43(12): 100473-100473. doi: 10.1016/j.cjsc.2024.100473
10. [10]
  Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
11. [11]
  Teng Wang , Jiachun Cao , Juan Li , Didi Li , Zhimin Ao . A novel photocatalytic mechanism of volatile organic compounds degradation on BaTiO₃ under visible light: Photo-electrons transfer from photocatalyst to pollutant. Chinese Chemical Letters, 2025, 36(3): 110078-. doi: 10.1016/j.cclet.2024.110078
12. [12]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
13. [13]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
14. [14]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
15. [15]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
16. [16]
  Guanyang Zeng , Xingqiang Liu , Liangqiao Wu , Zijie Meng , Debin Zeng , Changlin Yu . Novel visible-light-driven I- doped Bi2O2CO3 nano-sheets fabricated via an ion exchange route for dye and phenol removal. Chinese Journal of Structural Chemistry, 2024, 43(12): 100462-100462. doi: 10.1016/j.cjsc.2024.100462
17. [17]
  Jijoe Samuel Prabagar , Kumbam Lingeshwar Reddy , Dong-Kwon Lim . Visible-light responsive gold nanoparticle and nano-sized Bi2O3-x sheet heterozygote structure for efficient photocatalytic conversion of N2 to NH3. Chinese Journal of Structural Chemistry, 2025, 44(4): 100564-100564. doi: 10.1016/j.cjsc.2025.100564
18. [18]
  Hui Peng , Xiao Wang , Weiguo Huang , Shuiyue Yu , Linghang Kong , Qilin Wei , Jialong Zhao , Bingsuo Zou . Efficient tunable visible and near-infrared emission in Sb³⁺/Sm³⁺-codoped Cs₂NaLuCl₆ for near-infrared light-emitting diode, triple-mode fluorescence anti-counterfeiting and information encryption. Chinese Chemical Letters, 2024, 35(11): 109462-. doi: 10.1016/j.cclet.2023.109462
19. [19]
  Shiqi Peng , Yongfang Rao , Tan Li , Yufei Zhang , Jun-ji Cao , Shuncheng Lee , Yu Huang . Regulating the electronic structure of Ir single atoms by ZrO₂ nanoparticles for enhanced catalytic oxidation of formaldehyde at room temperature. Chinese Chemical Letters, 2024, 35(7): 109219-. doi: 10.1016/j.cclet.2023.109219
20. [20]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1143)
HTML views(106)

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

Visible light induced the high-efficiency spirocyclization reaction of propynamide and thiophenols via recyclable catalyst Pd/ZrO2

Metrics

通讯作者: 陈斌, bchen63@163.com

Visible light induced the high-efficiency spirocyclization reaction of propynamide and thiophenols via recyclable catalyst Pd/ZrO₂