Citation: Ma Xiaopan, Liu Fengping, Mo Dongliang. Recent Advances in Chan-Evans-Lam Coupling Reaction[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1069-1087. doi: 10.6023/cjoc201702001 shu

Recent Advances in Chan-Evans-Lam Coupling Reaction

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004

Corresponding author: Mo Dongliang, moeastlight@mailbox.gxnu.edu.cn
Received Date: 2 February 2017
Revised Date: 21 March 2017

Fund Project: the National Natural Science Foundation of China 21602037Natural Science Foundation of Guangxi No. 2016GXNSFFA380005the National Natural Science Foundation of China Nos. 21562005

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Chan-Evans-Lam reaction has been served as a powerful cross-coupling reaction in organic synthesis since its discovery in the 1990s owing to the feature of mild reaction conditions, functional group tolerance and open-flask chemistry. Up to now, it has been not only extensively utilized in carbon-heteroatom or carbon-carbon bonds formation, but also successfully applied to synthesize natural products and alkaloids. The new strategies of Chan-Evans-Lam reaction in organic synthesis as well as applications in total synthesis in recent five years are discussesed.
- coupling reaction,
- copper-catalyzed,
- organic boron reagents,
- carbon-heteroatom bond formation
1. [1]
  See reviews: (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
  (b) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
  (c) Mousseau, J. J.; Charette, A. B. Acc. Chem. Res. 2013, 46, 412.
  (d) Liu, C.; Liu, D.; Lei, A. Acc. Chem. Res. 2014, 47, 3459.
2. [2]
3. [3]
  (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
  (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
  (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
4. [4]
  (a) Ley, S. V.; Thomas, A. W. Angew. Chen., Int. Ed. 2003, 42, 5400.
  (b) Thomas, A. W.; Ley, S. V. In Modern Arylation Methods, Ed.: Ackermann, L., Wiley-VCH, Weinherim, 2008, p. 121.
5. [5]
  (a) Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids, Ed.: Hall, D. G., Wiley-VCH, Weinheim, 2005, Chapter 5, p. 205.
  (b) Li, J. J. In Name Recations: A Collection of Detailed Reaction Mechanisms and Synthetic Applications, 4th ed., Springer, New York, 2009, 102.
6. [6]
  (a) King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044.
  (b) King, A. E.; Ryland, B. L.; Brunold, T. C.; Stahl, S. S. Organometallics 2012, 31, 7948.
7. [7]
  Larsson, P. F.; Wallentin, C. J.; Norrby, P. O. ChemCatChem 2014, 6, 1277.
8. [8]
  Kumar, K. A.; Kannaboina, P.; Jaladanki, C. K.; Bharatam, P. V.; Das, P. ChemistrySelect 2016, 3, 601.
9. [9]
  Qiao, J. X.; Lam, P. Y. S. Synlett 2011, 829.
10. [10]
  Rao, K. S.; Wu, T. S. Tetrahedron 2012, 68, 7735. doi: 10.1016/j.tet.2012.06.015
11. [11]
  Bruneau, A.; Brion, J. D.; Alami, M.; Messaoudi, S. Chem. Commun. 2013, 49, 8359. doi: 10.1039/c3cc44780d
12. [12]
  Zhu, X.; Zhang, Q.; Su, W. RSC Adv. 2014, 4, 22775. doi: 10.1039/c4ra02952f
13. [13]
  Gogoi, A.; Sarmah, G.; Dewan, A.; Bora, U. Tetrahedron Lett. 2014, 55, 31. doi: 10.1016/j.tetlet.2013.10.084
14. [14]
  Rasheed, S.; Rao, D. N.; Reddy, K. R.; Aravinda, S.; Vishwakarma, R. A.; Das, P. RSC Adv. 2014, 4, 4960. doi: 10.1039/c3ra44903c
15. [15]
  Yoo, W. J.; Tsukamoto, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2015, 54, 6587. doi: 10.1002/anie.201500074
16. [16]
  Rasheed, S.; Rao, D. N.; Das, P. J. Org. Chem. 2015, 80, 9321. doi: 10.1021/acs.joc.5b01396
17. [17]
  Chen, J.; Natte, K.; Man, N. Y. T.; Stewart, S. G.; Wu, X. F. Tetrahedron Lett. 2015, 56, 4843. doi: 10.1016/j.tetlet.2015.06.092
18. [18]
  Rizwan, K.; Karakaya, I.; Heitz, D.; Zubair, M.; Rasool, N.; Molander, G. A. Tetrahedron Lett. 2015, 56, 6839. doi: 10.1016/j.tetlet.2015.10.080
19. [19]
  Mallia, C. J.; Burton, P. M.; Smith, A. M. R.; Walter, G. C.; Baxendale, L. R. Beilstein J. Org. Chem. 2016, 12, 1598. doi: 10.3762/bjoc.12.156
20. [20]
  Roy, S.; Sarma, M. J.; Kashyap, B.; Phukan, P. Chem. Commun. 2016, 52, 1170. doi: 10.1039/C5CC04619J
21. [21]
  Reddy, A. S.; Reddy, K. R.; Rao, D. N.; Jaladanki, C. K.; Bharatam, P. V.; Lam. P. Y. S.; Das, P. Org. Biomol. Chem. 2017, 15, 801. doi: 10.1039/C6OB02444K
22. [22]
  Vantourout, J. C.; Law, R. P.; Isidro-Llobet, A.; Atkinson, S. J.; Watson, A. J. B. J. Org. Chem. 2016, 81, 3942. doi: 10.1021/acs.joc.6b00466
23. [23]
  Krasavin, M. Eur. J. Med. Chem. 2015, 97, 525. doi: 10.1016/j.ejmech.2014.11.028
24. [24]
  Sarnpitak, P.; Mujumdar, P.; Morisseau, C.; Hwang, C. H.; Hammock, B.; Iurchenko, V.; Zozulya, S.; Gavalas, A.; Geronikaki, A.; Ivanenkov, Y.; Krasavin, M. Eur. J. Med. Chem. 2014, 84, 160. doi: 10.1016/j.ejmech.2014.07.023
25. [25]
  Darin, D.; Krasavin, M. J. Org. Chem. 2016, 81, 12514. doi: 10.1021/acs.joc.6b02404
26. [26]
  Onaka, T.; Umemoto, H.; Miki, Y.; Nakamura, A.; Maegawa, T. J. Org. Chem. 2014, 79, 6703. doi: 10.1021/jo500862t
27. [27]
  Boykin, D. W.; Farehat, A. A. Synth. Commun. 2015, 45, 245. doi: 10.1080/00397911.2014.961196
28. [28]
  Mandal, P. S.; Kumar, A. V. Synlett 2016, 27, 1408. doi: 10.1055/s-00000083
29. [29]
  Garnier, T.; Sakly, R.; Danel, M.; Chassaing, S.; Pale, P. Synthesis 2017, 49, 1223.
30. [30]
  Rao, D. N.; Rasheed, S.; Vishwakarma, R. A.; Das, P. Chem. Commun. 2014, 50, 12911. doi: 10.1039/C4CC05628K
31. [31]
  Beyer, A.; Castanheiro, T.; Busca, P.; Prestat, G. ChemCatChem 2015, 7, 2433. doi: 10.1002/cctc.201500510
32. [32]
  Rao, D. N.; Rasheed, S.; Kumar, K. A.; Reddy, A. S.; Das, P. Adv. Synth. Catal. 2016, 358, 2126. doi: 10.1002/adsc.v358.13
33. [33]
  Kumar, K. A.; Kannaboina, P.; Rao, D. N.; Das, P. Org. Biomol. Chem. 2016, 14, 8989. doi: 10.1039/C6OB01307D
34. [34]
  Nandi, G. C.; Kota, S. R.; Govender, T.; Kruger, H. G.; Arvidsson, P. I. Tetrahedron 2014, 70, 5428. doi: 10.1016/j.tet.2014.06.122
35. [35]
  Moon, S. Y.; Nam, J.; Rathwell, K.; Kim, W. S. Org. Lett. 2014, 16, 338. doi: 10.1021/ol403717f
36. [36]
  You, C.; Yao, F.; Yan, T.; Cai, M. RSC Adv. 2016, 6, 43605. doi: 10.1039/C6RA04298H
37. [37]
  Mo, D.-L.; Anderson, L. L. Angew. Chem., Int. Ed. 2013, 52, 6722. doi: 10.1002/anie.v52.26
38. [38]
  Mo, D.-L.; Wink, D. A.; Anderson, L. L. Org. Lett. 2012, 14, 5180. doi: 10.1021/ol3022885
39. [39]
  Kontokosta, D.; Mueller, D. S.; Mo, D.-L.; Pace, W. H.; Simpson, R. A.; Anderson, L. L. Beilstein J. Org. Chem. 2015, 11, 2097. doi: 10.3762/bjoc.11.226
40. [40]
  Ohata, J.; Minus, M. B.; Abernathy, M. E.; Ball, Z. T. J. Am. Chem. Soc. 2016, 138, 7472. doi: 10.1021/jacs.6b03390
41. [41]
  Rossi, S. A.; Shimkin, K. W.; Xu, Q.; Mori-Quiroz, L. M.; Watson, D. A. Org. Lett. 2013, 15, 2314. doi: 10.1021/ol401004r
42. [42]
  Racine, E.; Monnier, F.; Vors, J.-P.; Taillefer, M. Chem. Commun. 2013, 49, 7412. doi: 10.1039/c3cc42575d
43. [43]
  (a) Tabolin, A. A.; Ioffe, S. L. Chem. Rev. 2014, 114, 5426.
  (b) Shi, W.-M.; Ma, X.-P.; Su, G.-F.; Mo, D.-L. Org. Chem. Front. 2016, 3, 116.
44. [44]
  Mondal, M.; Sarmah, G.; Gogoi, K.; Bora, U. Tetrahedron Lett. 2012, 53, 6219. doi: 10.1016/j.tetlet.2012.09.003
45. [45]
  Mulla, S. A. R.; Chavan, S. S.; Inamdar, S. M.; Pathan, M. Y.; Shaikh, T. M. Y. Tetrahedron Lett. 2014, 55, 5327. doi: 10.1016/j.tetlet.2014.07.056
46. [46]
  Medda, A.; Pal, G.; Singha, R.; Hossain, T.; Saha, A.; Das, A, R. Synth. Commun. 2013, 43, 169. doi: 10.1080/00397911.2011.594544
47. [47]
48. [48]
  Wang, R.; Wang, L.; Zhang, K.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2015, 56, 4815. doi: 10.1016/j.tetlet.2015.06.066
49. [49]
  Khatib, M. E.; Molander, G. A. Org. Lett. 2014, 16, 4944. doi: 10.1021/ol5024689
50. [50]
  Marcum, J. S.; McGarry, K. A.; Ferber, C. J.; Clark, T. B. J. Org. Chem. 2016, 81, 7963. doi: 10.1021/acs.joc.6b01254
51. [51]
  Huang, F.; Quach, T. D.; Batey, R. A. Org. Lett. 2013, 15, 3150. doi: 10.1021/ol4013712
52. [52]
  Patil, A. S.; Mo, D.-L.; Wang, H. Y.; Mueller, D. S.; Anderson, L. L. Angew. Chem., Int. Ed. 2012, 51, 7799. doi: 10.1002/anie.201202704
53. [53]
  Wang, H. Y.; Anderson, L. L. Org. Lett. 2013, 15, 3362. doi: 10.1021/ol401416r
54. [54]
  Kontokosta, D.; Mueller, D. S.; Wang, H. Y.; Anderson, L. L. Org. Lett. 2013, 15, 4830. doi: 10.1021/ol402237w
55. [55]
  Xu, H. J.; Zhao, Y. Q.; Feng, T.; Feng, Y. S. J. Org. Chem. 2012, 77, 2878. doi: 10.1021/jo300100x
56. [56]
  Lin, Y.; Cai, M.; Fang, Z.; Zhao, H. Tetrahedron 2016, 72, 3335. doi: 10.1016/j.tet.2016.04.063
57. [57]
  Qian, Z.; Ge, N.; Jiang, X. Chem. Commun. 2015, 51, 10295. doi: 10.1039/C5CC03038B
58. [58]
  Xiao, X.; Feng, M.; Jiang, X. Angew. Chem., Int. Ed. 2016, 55, 14121. doi: 10.1002/anie.v55.45
59. [59]
  Koley, S.; Chowdhury, S.; Chanda, T.; Ramulu, B. J.; Anand, N.; Singh, M. S. Eur. J. Org. Chem. 2015, 409.
60. [60]
  Xu, J.; Xiao, B.; Xie, C. Q.; Luo, D. F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551. doi: 10.1002/anie.201206681
61. [61]
  Moon, P. J.; Halperin, H. M.; Lundgren, R. J. Angew. Chem., Int. Ed. 2016, 55, 1894. doi: 10.1002/anie.201510558
62. [62]
  Moon, P. J.; Yin, S. K.; Lundgren, R. J. J. Am. Chem. Soc. 2016, 138, 13826. doi: 10.1021/jacs.6b08906
63. [63]
  Li, H.; Tsu, C.; Blackburn, C.; Li, G.; Hales, P.; Dick, L.; Bogyo, M. J. Am. Chem. Soc. 2014, 136, 13562. doi: 10.1021/ja507692y
64. [64]
  Feng, Y.; Holte, D.; Zoller, J.; Umemiya, S.; Simke, L. R.; Baran. P. S. J. Am. Chem. Soc. 2015, 137, 10160. doi: 10.1021/jacs.5b07154
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