Citation: Duan Xiyan, Liu Ning, Wang Jia, Ma Junying. Progress in Copper-Catalyzed Chan-Lam Coupling of N-Compounds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 661-667. doi: 10.6023/cjoc201808015 shu

Progress in Copper-Catalyzed Chan-Lam Coupling of N-Compounds

School of Chemical Engineering & Pharmaceutics, Henan University of Science and Technology, Luoyang 471023

Corresponding author: Duan Xiyan, duanxiyan@tju.edu.cn
Received Date: 16 August 2018
Revised Date: 22 September 2018
Available Online: 26 March 2018
Fund Project: the Science and Technology Foundation of Henan Province 182102310106Project supported by the Science and Technology Foundation of Henan Province (No. 182102310106)

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Construction of C-N bond is one of the most important areas in synthetic organic chemistry and medical chemistry. Many synthetic methods for the construction of C-N bond have been reported over the past few years. Copper-catalyzed Chan-Lam reactions represent one of the most powerful and straightforward tools to construct C-N bonds. In this paper, the recent progress in Chan-Lam coupling of N-compounds with (hetero) aryl boronates to construct C-N bond based on the reaction mechanism, reaction system, the scope of substrates, etc., is reviewed.
- Chan-Lam coupling,
- copper-catalyzed,
- C-N bond,
- aryl boronates,
- N-compounds
1. [1]
  (a) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
  (b) Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13.
  (c) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
  (d) Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027.
  (e) Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27.
  (f) Crawford, S. M.; Lavery, C. B.; Stradiotto, M. Eur. Chem. J. 2013, 19, 16760.
  (g) Bruneau, A.; Roche, M.; Alami, M.; Messaoudi, S. ACS Catal. 2015, 5, 1386.
  (h) Gildner, P. G.; Colacot, T. J. Organometallics 2015, 34, 5497.
2. [2]
  (a) Hall, D. G. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed., Wiley-VCH, Weinheim, Germany, 2011.
  (b) Zhang, L.; Jiao, L. J. Am. Chem. Soc. 2017, 139, 607.
  (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
  (d) Ren, Y.; Tian, X.; Dong, C.; Zhao, S.; Wang, J.; Yan, M.; Qi, X.; Liu, G. Catal. Commun. 2013, 32, 15.
3. [3]
4. [4]
  Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933. doi: 10.1016/S0040-4039(98)00503-6
5. [5]
  Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P. D.; Chan, M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941. doi: 10.1016/S0040-4039(98)00504-8
6. [6]
  Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415. doi: 10.1016/S0040-4039(01)00510-X
7. [7]
  Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233. doi: 10.1021/ol000033j
8. [8]
  Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077. doi: 10.1021/ol0160396
9. [9]
  Sasaki, M.; Dalili, S.; Yudin, A. K. J. Org. Chem. 2003, 68, 2045. doi: 10.1021/jo020696+
10. [10]
  Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397. doi: 10.1021/ol035681s
11. [11]
  Moessner, C.; Bolm, C. Org. Lett. 2005, 7, 2667. doi: 10.1021/ol050816a
12. [12]
  Tao, C.-Z.; Cui, X.; Li, J.; Liu, A.-X.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 3525. doi: 10.1016/j.tetlet.2007.03.107
13. [13]
  Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48, 1114. doi: 10.1002/anie.v48:6
14. [14]
  Kianmehr, E.; Baghersad, M. H. Adv. Synth. Catal. 2011, 353, 2599. doi: 10.1002/adsc.v353.14/15
15. [15]
  Moon, S.-Y.; Nam, J.; Rathwell, K.; Kim, W.-S. Org. Lett. 2014, 16, 338. doi: 10.1021/ol403717f
16. [16]
  Moon, S.-Y.; Kim, U. B.; Sung, D.-B.; Kim, W.-S. J. Org. Chem. 2015, 80, 1856. doi: 10.1021/jo502828r
17. [17]
  Roy, S.; Sarma, M. J.; Kashyap, B.; Phukan, P. Chem. Commun. 2016, 52, 1170. doi: 10.1039/C5CC04619J
18. [18]
  Yoo, W.-J.; Tsukamoto, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2015, 54, 6587. doi: 10.1002/anie.201500074
19. [19]
  Liu, S.; Zu, W.; Zhang, J.; Xu, L. Org. Biomol. Chem., 2017, 15, 9288. doi: 10.1039/C7OB02491F
20. [20]
  Tao, C.; Liu, F.; Xu, B.; Cao, Z. J. Carbohydr. Chem. 2013, 32, 411. doi: 10.1080/07328303.2013.816851
21. [21]
  Ohata, J.; Minus, M. B.; Abernathy, M. E.; Ball, Z. T. J. Am. Chem. Soc. 2016, 138, 7472. doi: 10.1021/jacs.6b03390
22. [22]
  Lan, J.-B.; Chen, L.; Yu, X.-Q.; You, J.-S.; Xie, R.-G. Chem. Commun. 2004, 188. doi: 10.1039/b307734a
23. [23]
  Bakkestuen, K. A.; Gundersen, L. Tetrahedron Lett. 2003, 44, 3359. doi: 10.1016/S0040-4039(03)00576-8
24. [24]
  Wentzel, M. T.; Hewgley, J. B.; Kamble, R. M.; Wall, P. D.; Kozlowski, M. C. Adv. Synth. Catal. 2009, 351, 931. doi: 10.1002/adsc.v351:6
25. [25]
  Li, Y.; Gao, L.-X.; Han, F.-S. Chem. Commun. 2012, 48, 2719. doi: 10.1039/c2cc17894j
26. [26]
  Onaka, T.; Umemoto, H.; Miki, Y.; Nakamura, A.; Maegawa, T. J. Org. Chem. 2014, 79, 6703. doi: 10.1021/jo500862t
27. [27]
  Rao, D. N.; Rasheed, S.; Vishwakarma, R. A.; Das, P. Chem. Commun. 2014, 50, 12911. doi: 10.1039/C4CC05628K
28. [28]
  Dar'in D.; Krasavin, M. J. Org. Chem. 2016, 81, 12514. doi: 10.1021/acs.joc.6b02404
29. [29]
  Sahoo, H.; Mukherjee, S.; Grandhi, G. S.; Selvakumar, J.; Baidya, M. J. Org. Chem. 2017, 82, 2764. doi: 10.1021/acs.joc.7b00002
30. [30]
  Tzschucke, C.; Murphy, J.; Hartwig, J. F. Org. Lett. 2007, 9, 761. doi: 10.1021/ol062902w
31. [31]
  Sueki, S.; Kuninobu, Y. Org. Lett. 2013, 15, 1544. doi: 10.1021/ol400323z
32. [32]
  McGarry, K. A.; Duenas, A. A.; Clark, T. B. J. Org. Chem. 2015, 80, 7193. doi: 10.1021/acs.joc.5b01074
33. [33]
  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
34. [34]
  King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044. doi: 10.1021/ja9006657
35. [35]
  Vantourout, J. C.; Miras, H. N.; Isidro-Llobet, A.; Sproules, S.; Watson, A. J. B. J. Am. Chem. Soc. 2017, 139, 4769. doi: 10.1021/jacs.6b12800
36. [36]
  (a) Zhang, L.; Jiao, L. J. Am. Chem. Soc. 2017, 139, 607.
  (b) Larsen, M. A.; Wilson, C. V.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 8633.
  (c) Larsen, M. A.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 4287.
  (d) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305.
  (e) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
  (f) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
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