Citation: Liao Fumin, Yu Jinsheng, Zhou Jian. Recent Advances in the Highly Stereoselective Synthesis of Tri-or Tetra-substituted Monofluoroalkenes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2175-2186. doi: 10.6023/cjoc201705001 shu

Recent Advances in the Highly Stereoselective Synthesis of Tri-or Tetra-substituted Monofluoroalkenes

Liao Fumin ^a ,
Yu Jinsheng ^a,, ,
Zhou Jian ^a,b,,

a.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Yu Jinsheng, yujinsheng2011@163.com Zhou Jian, jzhou@chem.ecnu.edu.cn
Received Date: 1 May 2017
Revised Date: 28 June 2017
Available Online: 7 September 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21472049)the National Natural Science Foundation of China 21472049

Figures(25)

Monofluoroalkenes have found applications in many areas of research, including the design and development new materials and drug. The highly stereoselective synthesis of this privileged structural motif has attracted great synthetic attention. This review summarizes recent progresses in highly stereoselective synthesis of monofluoroalkenes from aldehydes, ketones and diazo compounds, other substrates such as alkynes, alkenyl metallic species and alkenes are also included. The advantages and disadvantages of different methods are discussed.
- monofluoroalkene,
- stereoselective synthesis,
- aldehyde and ketone,
- diazo compound
1. [1]
2. [2]
  (a) Hiyama, T. In Organofluorine Compounds:Chemistry and Ap-plications, Ed.:Yamamoto, H., Springer-Verlag, Berlin, 2000.
  (b) Fluorine in Medicinal Chemistry and Chemical Biology, Ojima, I. Ed.; Wiley-Blackwell:United Kingdom, 2009. For reaviews:
  (c) Bégué, J.-P.; Bonnet-Delphon, D. J. Fluorine Chem. 2006, 127, 992.
  (d) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
  (e) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
  (f) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
  (g) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
  (h) Jeschke, P. ChemBioChem 2004, 5, 570.
  (i) Pagliaro, M.; Ciriminna, R. J. Mater. Chem. 2005, 15, 4981.
  (j) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441.
3. [3]
  Thayer, A. M. Chem. Eng. News 2006, 84, 15.
4. [4]
  (a) Osada, S.; Sano, S.; Ueyama, M.; Chuman, Y.; Kodama, H.; Sakaguchi, K. Bioorg. Med. Chem. 2010, 18, 605.
  (b) Malo-Forest, M.; Landelle, G.; Roy, J.-A.; Lacroix, J.; Gaudreault, R.-C.; Paquin, J.-F. Bioorg. Med. Chem. Lett. 2013, 23, 1712.
  (c) Dutheuil, G.; Couve-Bonnaire, S.; Pannecoucke, X. Angew. Chem. Int. Ed. 2007, 46, 1290.
  (d) Wong, O. A.; Shi, Y. A. J. Org. Chem. 2009, 74, 8377.
  (e) Guérin, D.; Gaumont, A.-C.; Dez, I.; Mauduit, M.; Couve-Bonnaire, S.; Pannecoucke, X. ACS Catal. 2014, 4, 2374.
  (f) Dai, W.; Xiao, J.; Jin, G.; Wu, J.; Cao, S. J. Org. Chem. 2014, 79, 10537.
5. [5]
  (a) Shen, Q.; Huang, Y.-G.; Liu, C.; Xiao, J.-C.; Chen, Q.-Y.; Guo, Y. J. Fluorine Chem. 2015, 179, 14.
  (b) Tian, P.; Feng, C.; Loh, T.-P. Nat. Commun. 2015, 6, 7472.
  (c) Zhang, X.; Lin, Y.; Zhang, J.; Cao, S. RSC Adv. 2015, 5, 7905.
  (d) Wu, J.; Xiao, J.; Dai, W.; Cao, S. RSC Adv. 2015, 5, 34498.
  (e) Xiong, Y.; Huang, T.; Ji, X.; Wu, J.; Cao, S. Org. Biomol. Chem. 2015, 13, 7398.
  (f) Dai, W.; Shi, H.; Zhao, X.; Cao, S. Org. Lett. 2016, 18, 4284.
  (g) Kong, L.; Zhou, X.; Li, X. Org. Lett. 2016, 18, 6320.
6. [6]
  (a) Liu, G. Org. Biomol. Chem. 2012, 10, 6243.
  (b) Akana, J. A.; Bhattacharyya, K. X.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2007, 129, 7736.
  (c) Gorske, B. C.; Mbofana, C. T.; Miller, S. J. Org. Lett. 2009, 11, 4318.
  (d) Schuler, M.; Silva, F.; Bobbio, C.; Tessier, A.; Gouverneur, V. Angew. Chem. Int. Ed. 2008, 47, 7927.
  (e) de Haro, T.; Nevado, C. Chem. Commun. 2011, 47, 248;
  (f) Lan, Y.; Hammond, G. B. Org. Lett. 2002, 4, 2437.
  (g) Zhou, C.; Ma, Z.; Gu, Z.; Fu, C.; Ma, S. J. Org. Chem. 2008, 73, 772.
  (h) Cui, H. F.; Chai, Z.; Zhao, G.; Zhu, S. Z. Chin. J. Chem. 2009, 27, 189.
  (i) Lü, B.; Fu, C.; Ma, S. Org. Biomol. Chem. 2010, 8, 274.
7. [7]
  (a) Couve-Bonnaire, S.; Cahard, D.; Pannecoucke, X. Org. Biomol. Chem. 2007, 5, 1151.
  (b) Yanai, H.; Taguchi, T. Eur. J. Org. Chem. 2011, 5939.
  (c) Landelle, G.; Bergeron, M.; Turcotte-Savard, M.-O.; Paquin, J.-F. Chem. Soc. Rev. 2011, 40, 2867.
  (d) Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073.
  (e) Drouin, M.; Hamel, J.-D.; Paquin, J.-F. Synlett 2016, 27, 821.
  (f) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
8. [8]
  Schlosser, M.; Zimmermann, M. Synthesis 1969, 75.
9. [9]
  Cox, D. G.; Gurusamy, N.; Burton, D. J. J. Am. Chem. Soc. 1985, 107, 2811. doi: 10.1021/ja00295a046
10. [10]
  (a) Lei, X. S.; Dutheuil, G.; Pannecoucke, X.; Quirion, J. C. Org. Lett. 2004, 6, 2101.
  (b) Zoute, L.; Dutheuil, G.; Quirion, J.-C.; Jubault, P.; Pannecoucke, X. Synthesis 2006, 3409.
11. [11]
  Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641. doi: 10.1021/cr941140s
12. [12]
  Machleidt, H.; Wessendorf, R. Justus Liebigs Ann. Chem. 1964, 674, 1. doi: 10.1002/(ISSN)1099-0690
13. [13]
  Moghadam, G. E.; Penne, J. S. Bull. Soc. Chim. Fr. 1985, 448.
14. [14]
  Sano, S.; Matsumoto, T.; Nakao, M. Tetrahedron Lett. 2014, 55, 4480. doi: 10.1016/j.tetlet.2014.06.063
15. [15]
  Chevrie, D.; Lequeux, T.; Demoute, J. P.; Pazenok, S. Tetrahedron Lett. 2003, 44, 8127. doi: 10.1016/j.tetlet.2003.09.027
16. [16]
  Ghosh, A. K.; Zajc, B. Org. Lett. 2006, 8, 1553. doi: 10.1021/ol060002+
17. [17]
  (a) Zajc, B.; Kake, S. Org. Lett. 2006, 8, 4457.
  (b) Pfund, E.; Lebargy, C.; Rouden, J.; Lequeux, T. J. Org. Chem. 2007, 72, 7871.
18. [18]
  (a) Ghosh, A. K.; Banerjee, S.; Sinha, S.; Kang, S. B.; Zajc, B. J. Org. Chem. 2009, 74, 3689.
  (b) He, M.; Ghosh, A. K.; Zajc, B. Synlett 2008, 999.
19. [19]
  Alonso, D. A.; Fuensanta, M.; Gómez-Bengoa, E.; Nájera, C. Adv. Synth. Catal. 2008, 350, 1823. doi: 10.1002/adsc.v350:11/12
20. [20]
  Larnaud, F.; Pfund, E.; Linclau, B.; Lequeux, T. Tetrahedron 2014, 70, 5632. doi: 10.1016/j.tet.2014.06.081
21. [21]
  Zhao, Y.; Jiang, F.; Hu, J. J. Am. Chem. Soc. 2015, 137, 5199. doi: 10.1021/jacs.5b02112
22. [22]
  Satoh, T.; Itoh, N.; Onda, K.; Kitoh, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 2800. doi: 10.1246/bcsj.65.2800
23. [23]
  Chevrie, D.; Lequeux, T.; Pommelet, J.-C. Org. Lett. 1999, 1, 1539. doi: 10.1021/ol990178u
24. [24]
  Boys, M. L.; Collington, E. W.; Finch, H.; Swanson, S.; Whitehead, J. F. Tetrahedron Lett. 1988, 29, 3365. doi: 10.1016/0040-4039(88)85163-3
25. [25]
  (a) Zhang, W.; Huang, W.; Hu, J. Angew. Chem. Int. Ed. 2009, 48, 9858.
  (b) Shen, X.; Hu, J. Eur. J. Org. Chem. 2014, 4437.
  (c) Liu, Q.; Shen, X.; Ni, C.; Hu, J. Angew. Chem. Int. Ed. 2017, 56, 619.
26. [26]
  Welch, J. T.; Herbert, R. W. J. Org. Chem. 1990, 55, 4782. doi: 10.1021/jo00303a003
27. [27]
  Michida, M.; Mukaiyama, T. Chem. Lett. 2008, 37, 890. doi: 10.1246/cl.2008.890
28. [28]
  (a) Barma, D. K.; Kundeu, A.; Zhang, H.; Mioskowski, C.; Falck, J. R. J. Am. Chem. Soc. 2003, 125, 3218.
  (b) Falck, J. R.; Bojet, R.; Barma, D. K.; Bandyopadhyay, A.; Joseph, S.; Mioskowski, C. J. Org. Chem. 2006, 71, 8178.
  (c) Feng, Z.; Min, Q.-Q.; Zhao, H.-Y.; Gu, J.-W.; Zhang, X.Angew. Chem. Int. Ed. 2015, 54, 1270.
29. [29]
  Lemonnier, G.; Zoute, L.; Dupas, G.; Quirion, J.-C.; Jubault, P. J. Org. Chem. 2009, 74, 4124. doi: 10.1021/jo900422m
30. [30]
  Augustine, J.-K.; Bombrun, A.; Venkatachaliah, S.; Jothi, A. Org. Biomol. Chem. 2013, 11, 8065. doi: 10.1039/c3ob41592a
31. [31]
  Cao, C.-R.; Ou, S.; Jiang, M.; Liu, J.-T. Org. Biomol. Chem. 2014, 12, 467. doi: 10.1039/C3OB42093K
32. [32]
  (a) Grundmann, C. Justus. Liebigs Ann. Chem. 1938, 536, 29.
  (b) Font, J.; Serratosa, F.; Valls, J. Chem. Commun. 1970, 721.
  (c) Kulkowit, S.; McKervey, M. A. J. Chem. Soc., Chem. Commun. 1978, 1069.
  (d) Baratta, W.; Del Zotto, A.; Rigo, P. Chem. Commun. 1997, 2163.
  (e) Del Zotto, A.; Baratta, W.; Verardo, G.; Rigo, P. Eur. J. Org. Chem. 2000, 2795.
  (f) Doyle, M. P.; Hu, W.; Phillips, I. M. Org. Lett. 2000, 2, 1777.
  (g) Greenman, K. L.; Carter, D. S.; Van Vranken, D. L. Tetrahedron 2001, 57, 5219.
  (h) Doyle, M. P.; Yan, M. J. Org. Chem. 2002, 67, 602;
  (i) Li, G.-Y.; Che, C.-M. Org. Lett. 2004, 6, 1621.
  (j) Hodgson, D. M.; Angrish, D. Chem. Commun. 2005, 4902.
  (k) Chen, S.; Wang, J. Chem. Commun. 2008, 4198;
  (l) Xiao, Q.; Ma, J.; Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2009, 11, 4732.
  (m) Hansen, J. H.; Parr, B. T.; Pelphrey, P.; Jin, Q.; Autschbach, J.; Davies, H. M. L.Angew. Chem. Int. Ed. 2011, 50, 2544.
  (n) Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2012, 51, 5714.
  (o) Hu, M.; He, Z.; Gao, B.; Li, L.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2013, 135, 17302.
  (p) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236.
  (q) Zhang, D.; Xu, G.; Ding, D.; Zhu, C.; Li, J.; Sun, J. Angew. Chem. Int. Ed. 2014, 53, 11070.
  (r) Hu, M.; Ni, C.; Li, L.; Han, Y.; Hu, J. J. Am. Chem. Soc. 2015, 137, 14496.
  (s) Zhu, C.; Xu, G.; Liu, K.; Qiu, L.; Peng, S.; Sun, J. Chem. Commun. 2015, 51, 12768.
  (t) Zhu, C.; Xu, G.; Ding, D.; Qiu, L.; Sun, J. Org. Lett. 2015, 17, 4244.
  (u) Zhang, Z.; Yu, W.; Wu, C.; Wang, C.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2016, 55, 273.
  (v) Feng, S.; Mo, F.; Xia, Y.; Liu, Z.; Liu, Z.; Zhang, Y.; Wang, J. Angew. Chem. Int. Ed. 2016, 55, 15401.
33. [33]
  (a) Fuchigami, T.; Hayashi, T.; Konno, A. Tetrahedron Lett. 1992, 33, 3161.
  (b) Usuki, Y.; Iwaoka, M.; Tomoda, S. J. Chem. Soc., Chem. Commun. 1992, 1148.
34. [34]
  (a) Ivanova, M. V.; Bayle, A.; Besset, T.; Pannecoucke, X.; Poisson, T. Angew. Chem. Int. Ed. 2016, 55, 14141.
  (b) Feng, Z.; Min, Q.-Q.; Xiao, Y.-L.; Zhang, B.; Zhang, X.Angew. Chem. Int. Ed. 2014, 53, 1669.
35. [35]
  (a) Cao, Z.-Y.; Wang, X.; Tan, C.; Zhao, X.-L.; Zhou, J.; Ding, K. J. Am. Chem. Soc. 2013, 135, 8197.
  (b) Cao, Z.-Y.; Zhao, Y.-L.; Zhou, J. Chem. Commun. 2016, 52, 2537.
  (c) Zhao, Y.-L.; Cao, Z.-Y.; Zeng, X.-P.; Shi, J.-M.; Yu, Y.-H.; Zhou, J. Chem. Commun. 2016, 52, 3943.
36. [36]
  For a review, see:
  (a) Decostanzi, M.; Campagne, J.-M.; Leclerc, E. Org. Biomol. Chem. 2015, 13, 7351. For examples, see:
  (b) Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323.
  (c) Chu, L.; Zhang, X.; Qing, F.-L. Org. Lett. 2009, 11, 2197.
  (d) Yuan, Z.; Wei, Y.; Shi, M. Chin. J. Chem. 2010, 28, 1709.
  (e) Kashikura, W.; Mori, K.; Akiyama, T. Org. Lett. 2011, 13, 1860. For our continuous efforts in the functionalization of fluorinated enol silyl ethers, see:
  (f) Liu, Y.-L.; Zhou, J. Chem. Commun. 2012, 48, 1919.
  (g) Liu, Y.-L.; Zeng, X.-P.; Zhou, J. Acta Chim. Sinica. 2012, 70, 1451.
  (h) Liu, Y.-L.; Liao, F.-M.; Niu, Y.-F.; Zhao, X.-L.; Zhou, J. Org. Chem. Front. 2014, 1, 742.
  (i) Yu, J.-S.; Liu, Y.-L.; Tang, J.; Wang, X.; Zhou, J. Angew. Chem. Int. Ed. 2014, 53, 9512.
  (j) Liao, F.-M.; Liu, Y.-L.; Yu, J.-S.; Zhou, F.; Zhou, J. Org. Biomol. Chem. 2015, 13, 8906.
  (k) Yu, J.-S.; Zhou, J. Org. Biomol. Chem. 2015, 13, 10968.
  (l) Yu, J.-S.; Liao, F.-M.; Gao, W.-M.; Liao, K.; Zuo, R.-L.; Zhou, J. Angew. Chem. Int. Ed. 2015, 54, 7381.
  (m) Yu, J.-S.; Zhou, J. Org. Chem. Front. 2016, 3, 298.
  (n) Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730.
37. [37]
  Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem. Int. Ed. 2017, 56, 2459. doi: 10.1002/anie.201611625
38. [38]
  (a) Okoromoba, O. E.; Han, J.; Hammond, G. B.; Xu, B. J. Am. Chem. Soc. 2014, 136, 14381.
  (b) Nahra, F.; Patrick, S. R.; Bello, D.; Brill, M.; Obled, A.; Cordes, D. B.; Slawin, A. M. Z.; O'Hagan, D.; Nolan, S. P. ChemCatChem 2015, 7, 240.
  (c) Li, Y.; Liu, X.; Ma, D.; Liu, B.; Jiang, H. Adv. Synth. Catal. 2012, 354, 2683.
39. [39]
  (a) Lee, S. H.; Schwartz, J. J. Am. Chem. Soc. 1986, 108, 2445.
  (b) Tius, M. A.; Kawakami, J. K. Tetrahedron 1995, 51, 3997.
  (c) Sommer, H.; Fürstner A. Chem. Eur. J. 2017, 23, 558.
  (d) Petasis, N. A.; Yudin, A. K.; Zavialov, I. A.; Prakash, G. K. S.; Olah, G. A. Synlett 1997, 606.
  (e) Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860.
  (f) Tredwell, M.; Gourverneur, V. Org. Biomol. Chem. 2006, 4, 26.
  (g) Yang, M.-H.; Matikonda, S. S.; Altman, R. A. Org. Lett. 2013, 15, 3894.
  (h) Ye, Y.; Takada, T.; Buchwald, S. L. Angew. Chem. Int. Ed. 2016, 55, 15559.
40. [40]
  (a) Qiu, S.; Xu, T.; Zhou, J.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 2856;
  (b) Shao, Q.; Huang, Y. Chem. Commun. 2015, 51, 6584.
1. [1]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
2. [2]
  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
3. [3]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
4. [4]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
5. [5]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
6. [6]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
7. [7]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
8. [8]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
9. [9]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
10. [10]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
11. [11]
  Siwen Yuan , Qilin Wu , TianpengYin . NMR Spectroscopy Teaching Design Using the Mosher Method for Stereochemistry of Organic Compounds Based on BOPPPS Teaching Model. University Chemistry, 2025, 40(7): 161-168. doi: 10.12461/PKU.DXHX202502073
12. [12]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
13. [13]
  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
14. [14]
  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
15. [15]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
16. [16]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
17. [17]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
18. [18]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
19. [19]
  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
20. [20]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083

Get Citation

PDF

XML

Metrics

PDF Downloads(42)
Abstract views(4233)
HTML views(1421)

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