Citation: Li Gang, Chen Ye, Xia Jibao. Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 1949-1962. doi: 10.6023/cjoc201803013 shu

Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage

Li Gang ^a,b ,
Chen Ye ^a,, ,
Xia Jibao ^b,,

a.
School Chemistry of Chemical Engineering, Guizhou University, Guiyang 550025
b.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics(LICP), Chinese Academy of Sciences, Lanzhou 730000

Corresponding author: Chen Ye, ychen19@gzu.edu.cn Xia Jibao, jibaoxia@licp.cas.cn
Received Date: 12 March 2018
Revised Date: 8 April 2018
Available Online: 27 August 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21702212, 21772208, 21602230) and the Natural Science Foundation of Jiangsu Province (No. BK20161260)the National Natural Science Foundation of China 21602230the National Natural Science Foundation of China 21702212the Natural Science Foundation of Jiangsu Province BK20161260the National Natural Science Foundation of China 21772208

Figures(5)

Amines containing carbon-nitrogen (C-N) bonds are widely distributed in natural products, drug molecules and functional materials.C-N bonds are one of the most abundant and inert bonds in organic molecules.Selective cleavage of C-N bonds to construct carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds represents a new synthetic method in organic synthesis.It is difficult for the direct cleavage of C-N bond.Ammonium salts are a series of stable compounds easily obtained from amines.The recent progress of transition-metal-catalyzed cross-coupling reactions via C-N bond cleavage using ammonium salts as starting materials is summerized.
- transition-metal-catalysis,
- ammonium salt,
- cross-coupling reaction,
- C-N bond cleavage
1. [1]
  (a) Paul, F. ; Patt, J. ; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
  (b) Guram, A. S. ; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
  (c) Muci, A. R. ; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
  (d) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
2. [2]
  (a) Blanksby, S. J. ; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255.
  (b) Yao, X. -Q. ; Hou, X. -J. ; Jiao, H. ; Xiang, H. -W. ; Li, Y. -W. J. Phys. Chem. A 2003, 107, 9991.
3. [3]
  (a) Bonanno, J. B. ; Henry, T. P. ; Neithamer, D. R. ; Wolczanski, P. T. ; Lobkovsky, E. B. J. Am. Chem. Soc. 1996, 118, 5132.
  (b) Ueno, S. ; Chatani, N. ; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098.
  (c) Koreeda, T. ; Kochi, T. ; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 7238.
  (d) Tobisu, M. ; Nakamura, K. ; Chatani, N. J. Am. Chem. Soc. 2014, 136, 5587.
  (e) Zhao, Y. ; Snieckus, V. Org. Lett. 2014, 16, 3200.
  (f) Cong, X. ; Fan, F. ; Ma, P. ; Luo, M. ; Chen, H. ; Zeng, X. J. Am. Chem. Soc. 2017, 139, 15182.
4. [4]
  (a) Geng, W. ; Zhang, W. -X. ; Hao, W. ; Xi, Z. J. Am. Chem. Soc. 2012, 134, 20230.
  (b) Xie, Y. ; Hu, J. ; Wang, Y. ; Xia, C. ; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
  (c) Hao, W. ; Geng, W. ; Zhang, W. X. ; Xi, Z. Chem. -Eur. J. 2014, 20, 2605.
5. [5]
  Balz, G.; Schiemann, G.Ber.-Umweltbundesamt (Ger.) 1927, 60B, 1186.
6. [6]
  Brasen, W.R.; Hauser, C.R.Org.Synth.1954, 34, 58. doi: 10.15227/orgsyn.034.0058
7. [7]
8. [8]
  (a) Eds. : de Meijere, A. ; Diederich, F. ; Metal-Catalyzed CrossCoupling Reactions, Wiley-VCH, Weinheim, 2004, p. 437.
  (b) Eds. : de Meijere, A. ; Braese, S. ; Oestreich, M. Metal-Catalyzed Cross-Coupling Reactions And More, Wiley-VCH, Weinheim, 2014.
9. [9]
  Corriu, R.J.P.; Masse, J.P.J.Chem.Soc., Chem.Commun.1972, 144a.
10. [10]
  Tamao, K.; Sumitani, K.; Kumada, M.J.Am.Chem.Soc.1972, 94, 4374. doi: 10.1021/ja00767a075
11. [11]
  Terao, J.; Kambe, N.Acc.Chem.Res.2008, 41, 1545. doi: 10.1021/ar800138a
12. [12]
  Wenkert, E.; Han, A.-L.; Jenny, C.-J.J.Chem.Soc., Chem.Commun.1988, 975.
13. [13]
  (a) Wenkert, E. ; Michelotti, E. L. ; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
  (b) Yu, D. -G. ; Li, B. -J. ; Shi, Z. -J. Acc. Chem. Res. 2010, 43, 1486.
  (c) Rosen, B. M. ; Quasdorf, K. W. ; Wilson, D. A. ; Zhang, N. ; Resmerita, A. -M. ; Garg, N. K. ; Percec, V. Chem. Rev. 2011, 111, 1346.
  (d) Su, B. ; Cao, Z. -C. ; Shi, Z. -J. Acc. Chem. Res. 2015, 48, 886.
  (e) Tobisu, M. ; Chatani, N. Acc. Chem. Res. 2015, 48, 1717.
14. [14]
  (a) Clot, E. ; Eisenstein, O. ; Jasim, N. ; MacGregor, S. A. ; McGrady, J. E. ; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333.
  (b) Keyes, L. ; Love, J. A. RSC Catal. Ser. 2013, 11, 159.
  (c) Yang, S. -D. In Homogeneous Transition-Metal-Catalyzed C-F Sctivation, John Wiley & Sons, New York, 2015, pp. 203~268.
15. [15]
  Reeves, J.T.; Fandrick, D.R.; Tan, Z.; Song, J.J.; Lee, H.; Yee, N.K.; Senanayake, C.H.Org.Lett.2010, 12, 4388. doi: 10.1021/ol1018739
16. [16]
  Guo, W.-J.; Wang, Z.-X.Tetrahedron 2013, 69, 9580. doi: 10.1016/j.tet.2013.09.039
17. [17]
  Guisan-Ceinos, M.; Martin-Heras, V.; Tortosa, M.J.Am.Chem.Soc.2017, 139, 8448. doi: 10.1021/jacs.7b05273
18. [18]
  Ma, S.; Liu, Q.; Tang, X.; Cai, Y.Asian J.Org.Chem.2017, 6, 1209. doi: 10.1002/ajoc.v6.9
19. [19]
  (a) Dieck, H. A. ; Heck, R. F. J. Am. Chem. Soc. 1974, 96, 1133.
  (b) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
20. [20]
  Pan, Y.; Zhang, Z.; Hu, H.Synthesis 1995, 245.
21. [21]
  (a) Miyaura, N. ; Suzuki, A. Chem. Rev. 1995, 95, 2457.
  (b) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
22. [22]
  Blakey, S.B.; MacMillan, D.W.C.J.Am.Chem.Soc.2003, 125, 6046. doi: 10.1021/ja034908b
23. [23]
  Buszek, K.R.; Brown, N.Org.Lett.2007, 9, 707. doi: 10.1021/ol063027h
24. [24]
  de la Herrán, G.; Segura, A.; Csákÿ, A.G.Org.Lett.2007, 9, 961. doi: 10.1021/ol063042m
25. [25]
  Humphrey, G.R.; Kuethe, J.T.Chem.Rev.2006, 106, 2875. doi: 10.1021/cr0505270
26. [26]
  Maity, P.; Shacklady-McAtee, D.M.; Yap, G.P.A.; Sirianni, E.R.; Watson, M.P.J.Am.Chem.Soc.2013, 135, 280. doi: 10.1021/ja3089422
27. [27]
  Shacklady-McAtee, D.M.; Roberts, K.M.; Basch, C.H.; Song, Y.G.; Watson, M.P.Tetrahedron 2014, 70, 4257. doi: 10.1016/j.tet.2014.03.039
28. [28]
  Liu, X.-Y.; Zhu, H.-B.; Shen, Y.-J.; Jiang, J.; Tu, T.Chin.Chem.Lett.2017, 28, 350. doi: 10.1016/j.cclet.2016.09.006
29. [29]
  Wang, T.; Yang, S.; Xu, S.; Han, C.; Guo, G.; Zhao, J.RSC Adv.2017, 7, 15805. doi: 10.1039/C7RA02549A
30. [30]
  Turtscher, P.L.; Davis, H.J.; Phipps, R.J.Synthesis 2018, 50, 793. doi: 10.1055/s-0036-1588548
31. [31]
  Basch, C.H.; Liao, J.; Xu, J.; Piane, J.J.; Watson, M.P.J.Am.Chem.Soc.2017, 139, 5313. doi: 10.1021/jacs.7b02389
32. [32]
  (a) Katritzky, A. R. ; Gruntz, U. ; Kenny, D. H. ; Rezende, M. C. ; Sheikh, H. J. Chem. Soc., Perkin Trans. 1 1979, 430.
  (b) Katritzky, A. R. ; Marson, C. M. Angew. Chem., Int. Ed. 1984, 23, 420.
33. [33]
  (a) Shao, Z. ; Li, X. ; Chang, H. ; Wei, W. Chemistry 2013, 76, 704.
  (b) Dilman, A. D. ; Levin, V. V. Tetrahedron Lett. 2016, 57, 3986.
34. [34]
  Xie, L.G.; Wang, Z.X.Angew.Chem., Int.Ed.2011, 50, 4901. doi: 10.1002/anie.v50.21
35. [35]
  (a) Zhang, X. -Q. ; Wang, Z. -X. J. Org. Chem. 2012, 77, 3658.
  (b) Yang, X. ; Wang, Z. -X. Organometallics 2014, 33, 5863.
36. [36]
  Wang, D.-Y.; Morimoto, K.; Yang, Z.-K.; Wang, C.; Uchiyama, M.Chem.-Asian J.2017, 12, 2554. doi: 10.1002/asia.v12.19
37. [37]
  (a) Stille, J. K. Angew. Chem., Int. Ed. 1986, 25, 508.
  (b) Fugami, K. ; Kosugi, M. Top. Curr. Chem. 2002, 219, 87.
38. [38]
  Wang, D.-Y.; Kawahata, M.; Yang, Z.-K.; Miyamoto, K.; Komagawa, S.; Yamaguchi, K.; Wang, C.; Uchiyama, M.Nat.Commun.2016, 7, 12937. doi: 10.1038/ncomms12937
39. [39]
  Yamamura, M. ; Moritani, I. ; Murahashi, S. -I. J. Organomet. Chem. 1975, 91, C39.
  (b) Murahashi, S. ; Yamamura, M. ; Yanagisawa, K. ; Mita, N. ; Kondo, K. J. Org. Chem. 1979, 44, 2408.
  (c) Giannerini, M. ; Fañanás-Mastral, M. ; Feringa, B. L. Nat. Chem. 2013, 5, 667.
40. [40]
  Yang, Z.-K.; Wang, D.-Y.; Minami, H.; Ogawa, H.; Ozaki, T.; Saito, T.; Miyamoto, K.; Wang, C.; Uchiyama, M.Chem.-Eur.J.2016, 22, 15693. doi: 10.1002/chem.201603436
41. [41]
  He, F.; Wang, Z.-X.Tetrahedron 2017, 73, 4450. doi: 10.1016/j.tet.2017.06.004
42. [42]
  Ogawa, H.; Yang, Z.-K.; Minami, H.; Kojima, K.; Saito, T.; Wang, C.; Uchiyama, M.ACS Catal.2017, 7, 3988. doi: 10.1021/acscatal.7b01058
43. [43]
  Zhu, F.; Tao, J.-L.; Wang, Z.-X.Org.Lett.2015, 17, 4926. doi: 10.1021/acs.orglett.5b02458
44. [44]
  Yu, S.; Liu, S.; Lan, Y.; Wan, B.; Li, X.J.Am.Chem.Soc.2015, 137, 1623. doi: 10.1021/ja511796h
45. [45]
  Uemura, T.; Yamaguchi, M.; Chatani, N.Angew.Chem., Int.Ed.2016, 55, 3162. doi: 10.1002/anie.201511197
46. [46]
  Klauck, F.J.R.; James, M.J.; Glorius, F.Angew.Chem., Int.Ed.2017, 56, 12336. doi: 10.1002/anie.201706896
47. [47]
  Spettel, M.; Pollice, R.; Schnürch, M.Org.Lett.2017, 19, 4287. doi: 10.1021/acs.orglett.7b01946
48. [48]
  (a) Hofmann, A. W. Justus Liebigs Ann. Chem. 1851, 79, 11.
  (b) von Hofmann, A. W. Justus Liebigs Ann. Chem. 1851, 78, 253.
49. [49]
  Li, J.W.; Zheng, Z.J.; Xiao, T.T.; Xu, P.F.; Wei, H.Asian J.Org.Chem.2018, 7, 133. doi: 10.1002/ajoc.v7.1
50. [50]
  (a) Gambarotta, S. ; Alper, H. J. Organomet. Chem. 1980, 194, C19.
  (b) Lei, Y. ; Zhang, R. ; Wu, Q. ; Mei, H. ; Xiao, B. ; Li, G. J. Mol. Catal. A 2014, 381, 120.
  (c) Lei, Y. ; Zhang, R. ; Wu, L. ; Wu, Q. ; Mei, H. ; Li, G. Appl. Organomet. Chem. 2014, 28, 310.
51. [51]
  Moragas, T.; Gaydou, M.; Martin, R.Angew.Chem., Int.Ed.2016, 55, 5053. doi: 10.1002/anie.v55.16
52. [52]
  Zhang, X.-Q.; Wang, Z.-X.Org.Bioorg.Chem.2014, 12, 1448. doi: 10.1039/c3ob41989d
53. [53]
  Zhang, H.; Hagihara, S.; Itami, K.Chem.-Eur.J.2015, 21, 16796. doi: 10.1002/chem.v21.47
54. [54]
  Hu, J.; Sun, H.; Cai, W.; Pu, X.; Zhang, Y.; Shi, Z.J.Org.Chem.2016, 81, 14. doi: 10.1021/acs.joc.5b02557
55. [55]
  Basch, C.H.; Cobb, K.M.; Watson, M.P.Org.Lett.2016, 18, 136. doi: 10.1021/acs.orglett.5b03455
56. [56]
  Mfuh, A.M.; Doyle, J.D.; Chhetri, B.; Arman, H.D.; Larionov, O.V.J.Am.Chem.Soc.2016, 138, 2985. doi: 10.1021/jacs.6b01376
57. [57]
  (a) Said, S. A. ; Fiksdahl, A. Tetrahedron: Asymmetry 2001, 12, 1947.
  (b) Gui, Y. ; Tian, S. K. Org. Lett. 2017, 19, 1554.
  (c) Erika, B. ; Istvan, G. ; Gyorgy, K. Lett. Org. Chem. 2011, 8, 22.
58. [58]
  Lu, F.L.; Chen, Z.Y.; Li, Z.; Wang, X.Y.; Peng, X.Y.; Li, C.; Li, R.; Pei, H.Q.; Wang, H.M.; Gao, M.Asian J.Org.Chem.2018, 7, 141. doi: 10.1002/ajoc.v7.1
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