Citation: Dong Hao, Hou Meifang. Recent Progress in Synthesis of Amides[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 267-283. doi: 10.6023/cjoc201608014 shu

Recent Progress in Synthesis of Amides

Dong Hao ,
Hou Meifang ^*,,

School of Ecological Technology and Engineering, Shanghai Institute of Technology, Shanghai, 201400

Corresponding author: Hou Meifang, mfhou@sit.edu.cn
Received Date: 21 August 2016
Revised Date: 7 October 2016

Fund Project: the National Natural Science Foundation of China 41171250

Figures(31)

The formation of amide bond is one of the most key reactions in organic chemistry. How to generate amide bond economically is often overlooked as a contemporary challenge as a result of the widespread occurrence of amide polymers, natural products marketed drugs as well as synthetic intermediates. There are inherent drawbacks in the methods. Concerns about their waste and expense are becoming sharper. Thus, Novel chemical protocols to amide formation are being raised. Among a large amount of ways of preparing a amide bond, there has been a growing attention in the use of catalyzed methods for preparing such important functional group. In this review, the catalyst for the formation of an amide bond has become the highlight of some the latest literature in key areas. Alcohols, aldehydes, ketones, unsaturated hydrocarbons, etc., react with organic amines or inorganic amines under a variety of conditions to give the corresponding amide. The review of a new generation of amide-forming reactions may be beneficial to solving these problems.
- amides,
- catalyst,
- organic amine,
- ammonia
1. [1]
2. [2]
  Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 22. doi: 10.1038/480022a
3. [3]
  Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R. Green Chem. 2007, 9, 411. doi: 10.1039/B703488C
4. [4]
  Bantreil, X.; Fleith, C.; Martinez, J.; Lamaty, F. ChemCatChem 2012, 4, 1922. doi: 10.1002/cctc.201200441
5. [5]
  Ghosh, S. C.; Ngiam, J. S. Y.; Seayad, A. M.; Tuan, D. T.; Johannes, C. W.; Chen, A. Tetrahedron Lett. 2013, 54, 4922. doi: 10.1016/j.tetlet.2013.07.005
6. [6]
  Islam, S. M.; Molla, R. A.; Roy, S.; Ghosh, K. Appl. Organomet. Chem. 2014, 28, 900. doi: 10.1002/aoc.v28.12
7. [7]
  Hong, S. H.; Kim, K.; Kang, B. Tetrahedron 2015, 71, 4565. doi: 10.1016/j.tet.2015.02.016
8. [8]
  Rokade, B. V.; Gadde, K.; Prabhu, K. R. Eur. J. Org. Chem. 2015, (12), 2706.
9. [9]
  Wu, Z.; Hull, K. L. Chem. Sci. 2016, 7, 969. doi: 10.1039/C5SC03103F
10. [10]
  Hong, G.; Wu, S. Y.; Zhu, X. Y.; Mao, D.; Wang, L. M. Tetrahedron 2016, 72, 436. doi: 10.1016/j.tet.2015.11.063
11. [11]
  Yoo, W. J.; Li, C. J. J. Am. Chem. Soc. 2006, 128, 13064. doi: 10.1021/ja064315b
12. [12]
  Bode, J. W.; Sohn, S. S. J. Am. Chem. Soc. 2007, 129, 13798. doi: 10.1021/ja0768136
13. [13]
  Chiang, P. C.; Kim, Y. J.; Bode, J. W. Chem. Comm. 2009, 30, 4566.
14. [14]
  Leighty, M. W.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 15233. doi: 10.1021/ja306225u
15. [15]
  Luzzio, F. A. Tetrahedron 2001, 57, 915. doi: 10.1016/S0040-4020(00)00965-0
16. [16]
  Woog, M. K.; Li, G. L.; Kung, K. K. Chem. Commun. 2012, 48, 4112. doi: 10.1039/c2cc17689k
17. [17]
  Ambreen, N.; Wirth, T. Eur. J. Org. Chem. 2014, 34, 7590.
18. [18]
  (a) Heffner, J. E.; Brown, L. K.; Deleo, J. M. Am. J. Respir. Crit. Care Med. 1995, 151, 1700.
  (b) Sarkar, G.; Siddiqua, S. Eng. Geol. 2016, 202, 153.
19. [19]
  Ding, Y. Z.; Zhang, D. Y.; Zhang, X.; Chen, Y. T.; Wu, Z. B.; Wang, P. Y.; Xue, W.; Song, B. A.; Yang, S. Tetrahedron Lett. 2015, 56, 831. doi: 10.1016/j.tetlet.2014.12.113
20. [20]
  Lu, S. Y.; Badsara, S. S.; Wu, Y. C.; Reddy, D. M.; Lee, R. C. Tetrahedron Lett. 2016, 57, 633. doi: 10.1016/j.tetlet.2015.12.060
21. [21]
  Grzyb, J. B.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7485. doi: 10.1016/j.tetlet.2003.08.026
22. [22]
  Liebeskind, L. S.; Wu, W. T.; Zhang, Z. H. J. Am. Chem. Soc. 2011, 133, 14256. doi: 10.1021/ja2065158
23. [23]
  Townsend, S. D.; Wu, X. Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 10659. doi: 10.1021/ja303876e
24. [24]
  Vogel, P.; Zambron, B. K.; Dubbaka, S. R.; Markovic, D. Org. Lett. 2013, 15, 2550. doi: 10.1021/ol401053y
25. [25]
  Lipshutz, B. H.; Gabriel, C. M.; Keener, M.; Callou, F. Org. Lett. 2015, 17, 3968. doi: 10.1021/acs.orglett.5b01812
26. [26]
  Thiemann, T.; Jasem, Y. A.; Soom, N. A. C. R. Chimie 2016, 1.
27. [27]
  Kawahata, N. H.; Brookes, J.; Makara, G. M. Tetrahedron Lett. 2002, 43, 7221. doi: 10.1016/S0040-4039(02)01657-X
28. [28]
  Hosmane, R. S.; Ujjinamatada, R. K. Tetrahedron Lett. 2005, 46, 6005. doi: 10.1016/j.tetlet.2005.07.024
29. [29]
  An, D. K.; Jeon, A. R.; Kim, M. E.; Park, J. K.; Shin, W. K. Tetrahedron 2014, 70, 4420. doi: 10.1016/j.tet.2014.03.045
30. [30]
  Mecinovic, J.; Lenstra, D. C.; Nguyen, D. T. Tetrahedron 2015, 71, 5547. doi: 10.1016/j.tet.2015.06.066
31. [31]
  Wang, Q. W.; Yang, Y.; Fu, R. Z.; Ma, Y. S.; Yang, F.; Li, J. J.; Chai, W.; Yuan, R. X. Tetrahedron Lett. 2015, 56, 4527. doi: 10.1016/j.tetlet.2015.05.118
32. [32]
  Du, G. F.; Guo, H.; Wang, Y.; Dai, B. U.; He, L. Tetrahedron 2015, 71, 3472. doi: 10.1016/j.tet.2015.03.071
33. [33]
  Mizuno, N.; Yamaguchi, K.; Matsushita, M. Angew. Chem., Int. Ed. 2004, 43, 1576. doi: 10.1002/(ISSN)1521-3773
34. [34]
  Varma, R. S.; Polshettimar, V. Chem. Eur. J. 2009, 15, 1582. doi: 10.1002/chem.v15:7
35. [35]
  Kim, A. Y.; Bae, H. S.; Park, S. H; Park, S. K.; Park, R. H. Catal. Lett. 2011, 141, 685. doi: 10.1007/s10562-011-0561-y
36. [36]
  Shimizu, K. Z.; Imaiida, N.; Sawabe, K.; Satsuma. A. Appl. Catal., A 2012, 421~422, 114.
37. [37]
  Tyler, D. R.; Knapp, S. M. M.; Sherbow, T. J.; Yelle, R. B.; Juliette, J. Organometallics 2013, 32, 3744. doi: 10.1021/om400380j
38. [38]
  Qu, J. P.; Tong, P.; Yang, D. W.; Li, Y.; Wang, B. W. Organometallics 2015, 34, 3571. doi: 10.1021/acs.organomet.5b00387
39. [39]
  Jin, J. Y.; Etzion, R.; Santoso, B.; Yanaranop, P. Polymer 2016, 98, 244. doi: 10.1016/j.polymer.2016.06.041
40. [40]
  Alper, H.; Larksarp, C. J. Org. Chem. 2000, 65, 2773. doi: 10.1021/jo991922r
41. [41]
  Inoue, Y.; Tsukada, N.; Ohba, Y. J. Org. Chem. 2003, 687, 436. doi: 10.1016/j.jorganchem.2003.08.014
42. [42]
  Li, Z.; Ding, R. B.; Lu, Z.; Xiao, S. X.; Ma, X. L. J. Mol. Catal. A: Chem. 2006, 250, 100. doi: 10.1016/j.molcata.2006.01.056
43. [43]
  Crabtree, R. H.; Hull, J. F.; Hilton, S. T. Inorg. Chim. Acta 2010, 363, 1243. doi: 10.1016/j.ica.2009.08.022
44. [44]
45. [45]
  Deng, Y. Q.; Yin, S. F.; Au, C. T. lnd. Eng. Chem. Res. 2012, 51, 9492. doi: 10.1021/ie3001277
46. [46]
  Maronna, M. M.; Kruissink, E. C.; Tinge, J. T.; Agar, D. W.; Hoelderich, W. F. Ind. Eng. Chem. Res. 2016, 55, 1202. doi: 10.1021/acs.iecr.5b04240
47. [47]
  Shin, Y. Y.; Jung, D. J.; Lee, S. G. Catal. 2013, 3, 525.
48. [48]
  Mahajan, P. S.; Humne, V. T.; Tanpure, S. D.; Mhaske, S. B. Org. Lett. 2016, 18, 3450. doi: 10.1021/acs.orglett.6b01634
49. [49]
  Zhang, F.-L.; Wang, Y.-F.; Lonca, G. H.; Zhu, X.; Chiba, S. An-gew. Chem., Int. Ed. 2014, 53, 4390. doi: 10.1002/anie.201400938
50. [50]
  Zhu, X.; Wang, Y.-F.; Zhang, F.-L.; Chiba, S. Chem. Asian J. 2014, 9, 2458. doi: 10.1002/asia.201402421
51. [51]
  Zhang, F. L.; Zhu, X.; Chiba, S. Org. Lett. 2015, 17, 3138. doi: 10.1021/acs.orglett.5b01458
52. [52]
  Howell, A. R.; Chen, D. Tetrahedron Lett. 2015, 56, 3583. doi: 10.1016/j.tetlet.2015.02.133
53. [53]
  Lüdtke, D. S.; Silva, L.; Affeldt, R. F. J. Org. Chem. 2016, 81, 5464. doi: 10.1021/acs.joc.6b00832
54. [54]
  Babu, V. V. S.; Vasant, G-R.; Tantry, S. J. Tetrahedron Lett. 2005, 46, 4099. doi: 10.1016/j.tetlet.2005.04.007
55. [55]
  Li, Z. F.; Lai, G. Q.; Chen, W. F.; Li, K. B.; Hu, Z. Q.; Wang, L. L. Organometallics 2011, 30, 2026. doi: 10.1021/om200080f
56. [56]
  Liguori, A.; Siciliano, C.; Leggio, A.; Belsito, E. L.; Di, M. L.; Leotta, G. V.; Romio, E. Tetrahedron Lett. 2015, 56, 199. doi: 10.1016/j.tetlet.2014.11.067
57. [57]
  Gooßen, L. J.; Rauhaus, J. E.; Deng, G. Angew, Chem, Int. Ed. 2005, 44, 4042. doi: 10.1002/(ISSN)1521-3773
58. [58]
  Chang, S.; Kim, S. K.; Do, Y.; Lee, J.; Jung, D. Y.; Ahn, D.-S.; Lee, J. M. J. Am. Chem. Soc. 2006, 128, 12954. doi: 10.1021/ja0639315
59. [59]
  Takai, K.; Kuninobu, Y.; Salprima, Y. S. Org. Lett. 2007, 9, 5609. doi: 10.1021/ol702564e
60. [60]
  Beller, M.; Fang, X. J.; Jackstell, R. Angew, Chem., Int. Ed. 2013, 52, 14089. doi: 10.1002/anie.201308455
61. [61]
  Stephenson, N. A.; Zhu, J.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 10003. doi: 10.1021/ja8094262
62. [62]
  Srinivas, M.; Hudwekar, A. D.; Venkateswalu, V.; Reddy, G. L. Tetrahedron Lett. 2015, 56, 4775. doi: 10.1016/j.tetlet.2015.06.052
63. [63]
  Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917. doi: 10.1002/(ISSN)1521-3773
64. [64]
  Jin, X. J.; Ka, Z. Y.; Mizuno, N. Chem. Lett. 2012, 41, 866. doi: 10.1246/cl.2012.866
65. [65]
  Xu, S. X.; Liu, J. Q.; Hu, D. H.; Bi, X. H. Green Chem. 2015, 17, 184. doi: 10.1039/C4GC01328J
66. [66]
  Huang, H.; Tang, L. N.; Xi, Y.; He, G. K.; Zhu, H. J. Tetrahedron Lett. 2016, 57, 1873. doi: 10.1016/j.tetlet.2016.03.052
67. [67]
  Ohmura, R.; Takahata, M.; Togo, H. Tetrahedron Lett. 2010, 51, 4378. doi: 10.1016/j.tetlet.2010.06.051
68. [68]
  Yamaguchi, K.; Kobayashi, H.; Oishi, T.; Mizuno, N. Angew. Chem. 2012, 124, 559. doi: 10.1002/ange.201107110
69. [69]
  Wu, A.; Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J. Org. Lett. 2009, 11, 3810. doi: 10.1021/ol901250c
70. [70]
  Peng, Y. Q.; Song, G. H. Org. Prep. Proced. Int. 2002, 34, 95. doi: 10.1080/00304940209355747
71. [71]
  Ahmed, M.; Baburajan, P.; Sureshm, A. S. Tetrahedron Lett. 2015, 56, 4864. doi: 10.1016/j.tetlet.2015.06.054
72. [72]
  Wang, Y.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2012, 51, 7250. doi: 10.1002/anie.201203098
73. [73]
  Wang, T.; Yuan, L.; Zhao, Z.; Shao, A.; Gao, M.; Huang, Y.; Xiong, F.; Zhang, H.; Zhao, J. Green Chem. 2015, 17, 2741. doi: 10.1039/C5GC00299K
74. [74]
  Zhao, J.; Zhao, Z.; Wang, T.; Yuan, L.; Hu, X.; Xiong, F. Adv. Synth. Catal. 2015, 357, 2566. doi: 10.1002/adsc.201500310
75. [75]
  Griffin, J. M.; Atherton, J. H.; Page, M. I.; Powles, N. T. J. Phys. Org. Chem. 2016, 29, 768. doi: 10.1002/poc.v29.12
76. [76]
  Batra, S.; Dighe, S. U. Adv. Synth. Catal. 2016, 358, 500. doi: 10.1002/adsc.201500906
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