Citation: Yan Xiaojing, Li Chang, Jin Zhixiong, Xu Xiaofei, Chen Weiwei, Pan Yuanjiang. Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3837-3846. doi: 10.6023/cjoc202006043 shu

Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents

a.
Departement of Chemistry, Zhejiang University, Hangzhou 310027
b.
College of Life Science, Zhejiang Chinese Medical University, Hangzhou 310053

Corresponding author: Li Chang, lichang@zju.edu.cn Pan Yuanjiang, panyuanjiang@zju.edu.cn
Received Date: 21 June 2020
Revised Date: 9 August 2020
Available Online: 18 August 2020
Fund Project: the National Key R&D Program of China 2016YFF0200503the National Natural Science Foundation of China 21502168Project supported by the National Natural Science Foundation of China (Nos.21532005, 21502168) and the National Key R&D Program of China (No. 2016YFF0200503)the National Natural Science Foundation of China 21532005

Figures(5)

A catalytic system capable of selectively promoting the cyclopropanation reaction and C—S bond cleavage reaction was established. For the reactions between phenyl vinyl sulfide and diazoacetonitrile (generated by in situ method), the cyclopropanation reaction products were obtained under the catalysis of hemin chloride, and the C—S bond cleavage reaction products were generated in the presence of FePc. All the reations were operated without inert gas protection or high temperature, and the target products were obtained by stirring at room temperature for 1 h in moderate to excellent yields.
- hemin,
- diazo compound,
- sulfonium ylide,
- cyclopropanelation reaction,
- C-S bond cleavage reaction
1. [1]
  (a) Nguyen, T. B. Adv. Synth. Catal. 2017, 359, 1066.
  (b) Trost, B. M. Chem. Rev. 1978, 78, 363.
  (c) Trost, B. M. Acc. Chem. Res. 1978, 11, 453.
  (d) Ranu, B. C.; Jana, R. Adv. Synth. Catal. 2005, 347, 1811.
  (e) Peng, H. J.; Cheng, Y. F.; Ni, N. T.; Li, M. Y.; Choudhary, G.; Chou, H. T.; Lu, C. D.; Tai, P. C.; Wang, B. H. ChemMedChem 2009, 4, 1457.
  (f) Clayden, J.; MacLellan, P. Beilstein J. Org. Chem. 2011, 7, 582.
  (g)Landelle, G.; Panossian, A.; Leroux, F. R. Curr. Top. Med. Chem. 2014, 14, 941.
  (h) Screttas, C. G. J. Org. Chem. 1979, 44, 713.
  (i) Yin, J. M.; Pidgeon, C. Tetrahedron Lett. 1997, 38, 5953.
  (j) Couch, E. D.; Auvil, T. J.; Mattson, A. E. Chem.-Eur. J. 2014, 20, 8283.
  (k) Dairo, T. O.; Woo, L. K. Organometallics 2017, 36, 927.
2. [2]
  (a) Ahmed, K.; Saikia, G.; Paul, S.; Baruah, S. D.; Talukdar, H.; Sharma, M.; Islam, N. S. Tetrahedron 2019, 75, 130605.
  (b) Rayati, S.; Rezaie, S.; Nejabat, F. J. Coord. Chem. 2019, 72, 1466.
  (c) Gogoi, S. R.; Boruah, J. J.; Sengupta, G.; Saikia, G.; Ahmed, K.; Bania, K. K.; Islam, N. S. Catal. Sci. Technol. 2015, 5, 595.
  (d) Boruah, J. J.; Das, S. P.; Ankireddy, S. R.; Gogoi, S. R.; Islam, N. S. Green Chem. 2013, 15, 2944.
  (e) Tamami, B.; Yeganeh, H. Eur. Polym. J. 1999, 35, 1445.
  (f) Batigalhia, F.; Zaldini, H. M.; Ferreira, A. G.; Malvestiti, I.; Cass, Q. B. Tetrahedron 2001, 57, 9669.
  (g) Ghiron, A. F.; Thompson, R. C. Inorg. Chem. 1989, 28, 3647.
3. [3]
  (a) Hock, K. J.; Mertens, L.; Metze, F. K.; Schmittmann, C.; Koenigs, R. M. Green Chem. 2017, 19, 905.
  (b) Sun, C.-C.; Xu, K.; Zeng, C.-C. ACS Sustainable Chem. Eng. 2019, 7, 2255.
4. [4]
  (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
  (b) Kobayashi, S.; Komiyama, S.; Ishitani, H. Biotechnol. Bioeng. 1998, 61, 23.
  (c) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721.
5. [5]
  Trost, B. M.; Tanigawa, Y. J. Am. Chem. Soc. 1979, 101, 4743. doi: 10.1021/ja00510a059
6. [6]
  Guo, L.; Tu, H.-Y.; Zhu, S.; Chu, L. L. Org. Lett. 2019, 21, 4771. doi: 10.1021/acs.orglett.9b01658
7. [7]
  Seath, C. P.; Vogt, D. B.; Xu, Z.; Boyington, A. J.; Jui, N. T. J. Am. Chem. Soc. 2018, 140, 15525. doi: 10.1021/jacs.8b10238
8. [8]
  (a) Lo, J. C.; Gui, J. H.; Yabe, Y.; Pan, C. M.; Baran, P. S. Nature 2014, 516, 343.
  (b) Lo, J. C.; Kim, D.; Pan, C. M.; Edwards, J. T.; Yabe, Y.; Gui, J. H.; Qin, T.; Gutiérrez, S.; Giacoboni, J.; Smith, M. W.; Holland, P. L.; Baran, P. S. J. Am. Chem. Soc. 2017, 139, 2484.
9. [9]
  Debien, L.; Braun, M. G.; Quiclet, S. B.; Zard, S. Z. Org. Lett. 2013, 15, 6250. doi: 10.1021/ol403103u
10. [10]
  (a) Liu, J. G.; Ueda, M. J. Mater. Chem. 2009, 19, 8907.
  (b) Rodygin, K. S.; Ananikov, V. P. Green Chem. 2016, 18, 482.
11. [11]
  (a) Galardon, E.; Le, M. P.; Simonneaux, G. Tetrahedron 2000, 56, 615.
  (b) Patil, D. V.; Cavitt, M. A.; Grzybowski, P.; France, S. Chem. Commun. 2011, 47, 10278.
  (c) Chawner, S. J.; Cases, T. M. J.; Bull, J. A. Eur. J. Org. Chem. 2017, 5015.
  (d) Chandgude, A. L.; Fasan, R. Angew. Chem. Int. Ed. 2018, 57, 15852.
  (e) Tinoco, A.; Wei, Y.; Bacik, J. P.; Carminati, D. M.; Moore, E. J.; Ando, N.; Zhang, Y.; Fasan, R. ACS Catal. 2019, 9, 1514.
12. [12]
  Schmidt, C. D.; Kaschel, J.; Schneider, T. F.; Kratzert, D.; Stalke, D.; Werz, D. B. Org. Lett. 2013, 15, 6098. doi: 10.1021/ol402990j
13. [13]
  Gryko, D.; Giedyk, M.; Goliszewska, K.; ó Proinsias, K. Chem. Commun. 2016, 52, 1389. doi: 10.1039/C5CC07363D
14. [14]
  (a) Mehta, V. P.; Modha, S. G.; Van, E. E. J. Org. Chem. 2009, 74, 6870.
  (b) Kunchithapatham, K.; Eichman, C. C.; Stambuli, J. P. Chem. Commun. 2011, 47, 12679.
  (c) Empel, C.; Hock, K. J.; Koenigs, R. M. Chem. Commun. 2019, 55, 338.
  (d) Du, B. N.; Wang, W. M.; Wang, Y.; Qi, Z. H.; Tian, J. Q.; Zhou, J.; Wang, X. C.; Han, J. L.; Ma, J.; Pan, Y. Chem.-Asian J. 2018, 13, 404.
  (e) Ghosh, P.; Ganguly, B.; Perl, E.; Das, S. Tetrahedron Lett. 2017, 58, 2751.
  (f) Majouga, A. G.; Beloglazkina, E. K.; Moiseeva, A. A.; Shilova, O. V.; Manzheliy, E. A.; Lebedeva, M. A.; Davies, E. S.; Khlobystov, A. N.; Zyk, N. V. Dalton Trans. 2013, 42, 6290.
  (g) Desnoyer, A. N.; Love, J. A. Chem. Soc. Rev. 2017, 46, 197.
15. [15]
  (a) Sun, R.; Du, Y.; Tian, C.; Li, L.; Wang, H.; Zhao, Y. L. Adv. Syn. Catal. 2019, 361, 5684.
  (b) Yan, X. J.; Li, C.; Xu, X. F.; He, Q.; Zhao, X. Y.; Pan, Y. J. Tetrahedron 2019, 75, 3081.
  (c) Yan, X. J.; Li, C.; Xu, X. F.; Zhao, X. Y.; Pan, Y. J. Adv. Synth. Catal. 2020, 362, 2005.
16. [16]
  (a) Schmink, J. R.; Dockrey, S. A. B.; Zhang, T. Y.; Chebet, N.; Venrooy, A.; Sexton, M.; Lew, S. I.; Chou, S.; Okazaki, A. Org. Lett. 2016, 6360.
  (b) Liu, T, Qiu, R. H.; Zhu, L. Z.; Yin, S. F.; Au, C. T.; Kambe, N. Chem.-Asian J. 2018, 13, 3833.
  (c) Matt, C.; Kölblin, F.; Streuff, J. Org. Lett. 2019, 21, 6983.
17. [17]
  Xu, X. F.; Li, C.; Tao, Z. H.; Pan, Y. J. Adv. Synth. Catal. 2015, 357, 3341. doi: 10.1002/adsc.201500418
18. [18]
  Xu, X. F.; Li, C.; Tao, Z. H.; Pan, Y. J. Green Chem. 2017, 19, 1245. doi: 10.1039/C6GC02681H
19. [19]
  Xu, X. F.; Li, C.; Xiong, M. T.; Tao, Z. H.; Pan, Y. J. Chem. Commun. 2017, 53, 6219. doi: 10.1039/C7CC02484C
20. [20]
  Fu, Y.; Zhang, Y. L.; Gao, Z. H.; Wu, Y. Z.; Zhong, F. R. Org. Biomol. Chem. 2019, 17, 9994. doi: 10.1039/C9OB02151E
21. [21]
  (a) Vargas, D. A.; Tinoco, A.; Tyagi, V.; Fasan, R. Angew. Chem. Int. Ed. 2018, 57, 9911.
  (b) Brandenberg, O. F.; Chen, K.; Arnold, F. H. J. Am. Chem. Soc. 2019, 141, 8989.
  (c) Sreenilayam, G.; Fasan, R. Chem. Commun. 2015, 51, 1532.
  (d) Lewis, R. D.; Garcia, B. M.; Chalkley, M. J.; Buller, A. R.; Houk. K. N.; Jennifer Kan, S. B.; Arnold, F. H. Proc. Natl. Acad. Sci. 2018, 115, 7308.
  (e) Kan, S. B. J.; Lewis, R. D.; Chen, K.; Arnold, F. H. Science 2016, 354, 1048.
22. [22]
  (a) Curtius, T. Ber. Dtsch. Chem. Ges. 1898, 31, 2489.
  (b) Mykhailiuk, P. K. Eur. J. Org. Chem. 2015, 2015, 7235.
  (c) Empel, C.; Hock, K. J.; Koenigs, R. M. Org. Biomol. Chem. 2018, 16, 7129.
23. [23]
  Mykhailiuk, P. K.; Koenigs, R. M. Chem.-Eur. J., 2020, 26, 89. doi: 10.1002/chem.201903335
24. [24]
  (a) Renata, H.; Lewis, R. D.; Sweredoski, M. J.; Moradian, A.; Hess, S.; Wang, Z. J.; Arnold, F. H. J. Am. Chem. Soc. 2016, 138, 12527.
  (b) Li, Y.; Huang, J. S.; Zhou, Z. Y.; Che, C. M.; You, X. Z. J. Am. Chem. Soc. 2002, 124, 13185.
25. [25]
  (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
  (b) Melvin, L. S. Sulfur Ylides: Emerging Synthetic Intermediates, Academic Press, New York, 1975.
26. [26]
  Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124, 1590. doi: 10.1021/ja0173932
1. [1]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
2. [2]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
3. [3]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
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]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
6. [6]
  Qiwen Chen , Baolei Wang . Research Progress on One-Electron σ-Bond of Organic Compounds. University Chemistry, 2025, 40(11): 191-198. doi: 10.12461/PKU.DXHX202412136
7. [7]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . Optimizing interfacial electric fields in carbon nitride nanosheet/spherical conjugated polymer S-scheme heterojunction for hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-0. doi: 10.1016/j.actphy.2025.100095
8. [8]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
9. [9]
  Linlin Wu , Yonghua Zhou , Zhongbei Li , Liu Deng , Younian Liu , Limiao Chen , Jianhan Huang . Digital Education Promoting Applied Chemistry Comprehensive Experiments: A Case Study of Catalytic Oxidation of Hydrogen Chloride and Reaction Kinetics. University Chemistry, 2025, 40(9): 273-278. doi: 10.12461/PKU.DXHX202411018
10. [10]
  Shikun Jia , Hui Jiang , Yuanyuan Chang , Linlin Shi , Erqing Li , Kai Li , Xinqi Hao , Guangjian Mei . 大学有机化学“芳香性”教学拓展——以芳香全氮化合物为例. University Chemistry, 2026, 41(10): 127-131. doi: 10.12461/PKU.DXHX202511012
11. [11]
  Tong TAO , Shufeng ZHANG , Feifan LANG , Chunyan NI , Bing WU , Jianping LANG . Synthesis, structures, and daylight-induced [2+2] cycloaddition reactivity of two Cd(Ⅱ)-based pillared-layer coordination polymers. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1121-1130. doi: 10.11862/CJIC.20260115
12. [12]
  Ying Wang , Mingcheng Yang , Zhu Yin , Yingqi Wang , Jiajia Cheng . Transition metal-free poly(heptazine imide) photocatalyst for C-X bond construction from katritzky salts. Acta Physico-Chimica Sinica, 2026, 42(7): 100212-. doi: 10.1016/j.actphy.2025.100212
13. [13]
  Linjie Wang , Zhao Wei , Ming Gao , Xiaohui Zheng , Xinghai Hao . Item Development in the Context of Academic Exploration: Materials, Key Considerations, and Suggestions: A Case Study on the Research and Development of Polynitrogen Compounds. University Chemistry, 2026, 41(2): 411-419. doi: 10.12461/PKU.DXHX202503033
14. [14]
  Junjie Zhang , Jinke Li , Chaochao Dong , Jiawen Guo , Yue Wang , Yingxin Shui . 数字化技术在共轭聚合物探针检测全氟烷基化合物中的应用——微观机理探究与可视定量分析. University Chemistry, 2026, 41(10): 226-238. doi: 10.12461/PKU.DXHX202509092
15. [15]
  Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
16. [16]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
17. [17]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
18. [18]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-0. doi: 10.3866/PKU.WHXB202408015
19. [19]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
20. [20]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205

Get Citation

PDF

XML

Metrics

PDF Downloads(27)
Abstract views(8109)
HTML views(1179)

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