Citation: Zhang Hao, Yu Shouyun. Visible Light-Promoted Isomerization of Alkenes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 95-108. doi: 10.6023/cjoc201809010 shu

Visible Light-Promoted Isomerization of Alkenes

Zhang Hao ^a,b ,
Yu Shouyun ^b,,

a.
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002
b.
State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023

Corresponding author: Yu Shouyun, yushouyun@nju.edu.cn
Received Date: 6 September 2018
Revised Date: 14 October 2018
Available Online: 19 January 2018
Fund Project: the National Natural Science Foundation of China (No. 21732003) 21732003Project supported by the National Natural Science Foundation of China (No. 21732003)

Figures(25)

The traditional methods for synthesizing Z-olefins generally require the use of high-energy reagents. These methods are usually controlled by kinetics. The reaction conditions are harsh and low atom economic. During the process of separation, Z-olefins are easy to convert to the thermodynamically more stable E-olefins. With the continuous development of organic photochemistry and photocatalysis technology, more and more synthetic challenges have been solved by photocatalysis. Herein, various types of visible light-promoted photocatalytic isomerization of olefins are reviewed.
- photochemistry,
- olefins,
- isomerization,
- energy transfer
1. [1]
2. [2]
  (a) Wittig, G.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44.
  (b) Bergelson, L. D.; Shemyakin, M. M. Tetrahedron 1963, 19, 149.
  (c) Dong, D. J.; Li, H.-H.; Tian, S.-K. J. Am. Chem. Soc. 2010, 132, 5018.
3. [3]
  (a) Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 14, 4833.
  (b) Yao, C.-Z.; Li, Q.-Q.; Wang, M.-M.; Ning, X.-S.; Kang, Y.-B. Chem. Commun. 2015, 51, 7729.
4. [4]
  (a) Peterson, D. J. J. Org. Chem. 1968, 33, 780.
  (b) Staden, L. F. V.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195.
5. [5]
  (a) Koh, M. J.; Khan, R. K. M.; Torker, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2014, 53, 1968.
  (b) Quigley, B. L.; Grubbs, R. H. Chem. Sci. 2013, 5, 501.
  (c) Gottumukkala, A. L.; Madduri, A. V. R.; Minnaard, A. J. ChemCatChem 2012, 4, 462.
  (d) Meek, S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471, 461.
  (e) Endo, K.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 8525.
6. [6]
  (a) Lindlar, H. Helv. Chim. Acta 1952, 35, 446.
  (b) Li, X.; Song, W.; Tang, W. J. Am. Chem. Soc. 2013, 135, 16797.
  (c) Song, W.; Li, X.; Yang, K.; Zhao, X.-L.; Glazier, D. A.; Xi, B.-M.; Tang, W. J. Org. Chem. 2016, 81, 2930.
7. [7]
  Singh, K.; Staig, S. J.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 5275. doi: 10.1021/ja5019749
8. [8]
  Cai, W.; Fan, H.; Ding, D.; Zhang, Y.; Wang, W. Chem. Commun. 2017, 53, 12918. doi: 10.1039/C7CC07984B
9. [9]
  (a) Wald, G. J. Gen. Physiol. 1935, 19, 351.
  (b) O'Leary, B.; Duke, B.; Eilers, J. E. Nature 1973, 246, 166.
  (c) Lion, F.; Rotmans, J. P.; Daemen, F. J. M.; Bonting, S. L. Biochim. Biophys. Acta 1975, 384, 283.
  (d) Gai, F.; Hasson, K. C.; Cooper McDonald, J.; Anfinrud, P. A. Science 1998, 279, 1886.
  (e) Rando, R. R. Chem. Rev. 2001, 101, 1881.
  (f) Strauss, O. Physiol. Rev. 2005, 85, 845.
  (g) Redmond, T. M.; Poliakov, E.; Yu, S.; Tsai, J.-Y.; Lu, Z.; Gentleman, S. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 13658.
10. [10]
  Metternich, J. B.; Gilmour, R. Synlett 2016, 27, 2541. doi: 10.1055/s-0036-1588621
11. [11]
  (a) Metternich, J. B.; Gilmour, R. J. Am. Chem. Soc. 2015, 137, 11254.
  (b) Metternich, J. B.; Artiukhin, D. G.; Holland, M. C.; Bremen-Kühne, M. V.; Neugebauer, J.; Gilmour, R. J. Org. Chem. 2017, 82, 9955.
12. [12]
  Walker, A. G.; Radda, G. K. Nature 1967, 215, 1483.
13. [13]
  Metternich, J. B.; Gilmour, R. J. Am. Chem. Soc. 2015, 137, 11254. doi: 10.1021/jacs.5b07136
14. [14]
  Metternich, J. B.; Gilmour, R. J. Am. Chem. Soc. 2016, 138, 1040. doi: 10.1021/jacs.5b12081
15. [15]
  Metternich, J. B.; Artiukhin, D. G.; Holland, M. C.; Bremen-Kühne, M. V.; Neugebauer, J.; Gilmour, R. J. Org. Chem. 2017, 82, 9955. doi: 10.1021/acs.joc.7b01281
16. [16]
  Metternich, J. B.; Sagebiel, S.; Lückener, A.; Lamping, S.; Ravoo, B. J.; Gilmour, R. Chem.-Eur. J. 2018, 24, 4228. doi: 10.1002/chem.v24.17
17. [17]
  Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.; Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197. doi: 10.1021/ja01070a002
18. [18]
  (a) Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1962, 84, 4983.
  (b) Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1963, 85, 2515.
  (c) Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.; Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197.
19. [19]
  (a) Arai, T.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1980, 9, 261.
  (b) Arai, T.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2204.
20. [20]
  Zhao, Y.-P.; Yang, L.-Y.; Liu, R. S. H. Green Chem. 2009, 11, 837. doi: 10.1039/b819207c
21. [21]
  Cai, W.; Fan, H.; Ding, D.; Zhang, Y.; Wang, W. Chem. Commun. 2017, 53, 12918. doi: 10.1039/C7CC07984B
22. [22]
  Faßbender, S. I.; Metternich, J. B.; Gilmour, R. Org. Lett. 2018, 20, 724. doi: 10.1021/acs.orglett.7b03859
23. [23]
  Osawa, M.; Hoshino, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 2001, 40, 18.
24. [24]
  Rackl, D.; Kreitmeier, P.; Reiser, O. Green Chem. 2016, 18, 214. doi: 10.1039/C5GC01792K
25. [25]
  Fabry, D. C.; Ronge, M. A.; Rueping, M. Chem. Eur. J. 2015, 21, 5350. doi: 10.1002/chem.201406653
26. [26]
  Molloy, J. J.; Metternich, J. B.; Daniliuc, C. G.; Watson, A. J. B.; Gilmour, R. Angew. Chem., Int. Ed. 2018, 57, 3168. doi: 10.1002/anie.201800286
27. [27]
  Lin, Q.-Y.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2014, 79, 10434. doi: 10.1021/jo502040t
28. [28]
  Iqbal, N.; Jung, J.; Park, S.; Cho, E. J. Angew. Chem., Int. Ed. 2014, 53, 539. doi: 10.1002/anie.v53.2
29. [29]
  Senaweera, S. M.; Singh, A.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 3002. doi: 10.1021/ja500031m
30. [30]
  (a) Singh, A.; Kubik, J. J.; Weaver, J. D. Chem. Sci. 2015, 6, 7206.
  (b) Senaweera, S.; Weaver, J. D. J. Am. Chem. Soc. 2016, 138, 2520.
31. [31]
  Singh, A.; Fennell, C. J.; Weaver, J. D. Chem. Sci. 2016, 7, 6796. doi: 10.1039/C6SC02422J
32. [32]
  Zhang, H.; Huang, X. Adv. Synth. Catal. 2016, 358, 3736. doi: 10.1002/adsc.201600704
33. [33]
  Li, Y.; Miao, T.; Li, P.; Wang, L. Org. Lett. 2018, 20, 1735. doi: 10.1021/acs.orglett.8b00171
34. [34]
  Zheng, C.; Cheng, W.-M.; Li, H.-L.; Na, R.-S.; Shang, R. Org. Lett. 2018, 20, 2559. doi: 10.1021/acs.orglett.8b00712
35. [35]
  Li, J.; Chen, J.; Huang, W.; Cheng, X. Chin. J. Org. Chem. 2018, 38, 1507.
36. [36]
  An, X.-D.; Zhang, H.; Xu, Q.; Yu, L.; Yu, S. Chin. J. Chem. 2018, 36, 1147. doi: 10.1002/cjoc.v36.12
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