REVIEW

Recent Progress in Synthesis of Amides

  • Dong Hao ,
  • Hou Meifang
Expand
  • School of Ecological Technology and Engineering, Shanghai Institute of Technology, Shanghai, 201400

Received date: 2016-08-21

  Revised date: 2016-10-07

  Online published: 2016-11-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 41171250).

Abstract

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.

Cite this article

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

References

[1] (a) Qin, W. W.; Liu, B.; Ma, J. Chin. J. Org. Chem. 2012, 32, 896 (in Chinese).(秦伟伟, 刘波, 马静, 有机化学, 2012, 32, 896.)
(b) Burwell, D. A.; Thompson, M. E. Chem. Mater. 1991, 3, 730.
(c) Barrett, A. G. M.; Patel, B. H. J. Org. Chem. 2012, 77, 11296.
(d) Yin, L. A.; Brewitz, L.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2014, 136, 17958.
[2] Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 22.
[3] Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R. Green Chem. 2007, 9, 411.
[4] Bantreil, X.; Fleith, C.; Martinez, J.; Lamaty, F. ChemCatChem 2012, 4, 1922.
[5] Ghosh, S. C.; Ngiam, J. S. Y.; Seayad, A. M.; Tuan, D. T.; Johannes, C. W.; Chen, A. Tetrahedron Lett. 2013, 54, 4922.
[6] Islam, S. M.; Molla, R. A.; Roy, S.; Ghosh, K. Appl. Organomet. Chem. 2014, 28, 900.
[7] Hong, S. H.; Kim, K.; Kang, B. Tetrahedron 2015, 71, 4565.
[8] Rokade, B. V.; Gadde, K.; Prabhu, K. R. Eur. J. Org. Chem. 2015, (12), 2706.
[9] Wu, Z.; Hull, K. L. Chem. Sci. 2016, 7, 969.
[10] Hong, G.; Wu, S. Y.; Zhu, X. Y.; Mao, D.; Wang, L. M. Tetrahedron 2016, 72, 436.
[11] Yoo, W. J.; Li, C. J. J. Am. Chem. Soc. 2006, 128, 13064.
[12] Bode, J. W.; Sohn, S. S. J. Am. Chem. Soc. 2007, 129, 13798.
[13] Chiang, P. C.; Kim, Y. J.; Bode, J. W. Chem. Comm. 2009, 30, 4566.
[14] Leighty, M. W.; Shen, B.; Johnston, J. N. J. Am. Chem. Soc. 2012, 134, 15233.
[15] Luzzio, F. A. Tetrahedron 2001, 57, 915.
[16] Woog, M. K.; Li, G. L.; Kung, K. K. Chem. Commun. 2012, 48, 4112.
[17] Ambreen, N.; Wirth, T. Eur. J. Org. Chem. 2014, 34, 7590.
[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] 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.
[20] Lu, S. Y.; Badsara, S. S.; Wu, Y. C.; Reddy, D. M.; Lee, R. C. Tetrahedron Lett. 2016, 57, 633.
[21] Grzyb, J. B.; Batey, R. A. Tetrahedron Lett. 2003, 44, 7485.
[22] Liebeskind, L. S.; Wu, W. T.; Zhang, Z. H. J. Am. Chem. Soc. 2011, 133, 14256.
[23] Townsend, S. D.; Wu, X. Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 10659.
[24] Vogel, P.; Zambron, B. K.; Dubbaka, S. R.; Markovic, D. Org. Lett. 2013, 15, 2550.
[25] Lipshutz, B. H.; Gabriel, C. M.; Keener, M.; Callou, F. Org. Lett. 2015, 17, 3968.
[26] Thiemann, T.; Jasem, Y. A.; Soom, N. A. C. R. Chimie 2016, 1.
[27] Kawahata, N. H.; Brookes, J.; Makara, G. M. Tetrahedron Lett. 2002, 43, 7221.
[28] Hosmane, R. S.; Ujjinamatada, R. K. Tetrahedron Lett. 2005, 46, 6005.
[29] An, D. K.; Jeon, A. R.; Kim, M. E.; Park, J. K.; Shin, W. K. Tetrahedron 2014, 70, 4420.
[30] Mecinovic, J.; Lenstra, D. C.; Nguyen, D. T. Tetrahedron 2015, 71, 5547.
[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.
[32] Du, G. F.; Guo, H.; Wang, Y.; Dai, B. U.; He, L. Tetrahedron 2015, 71, 3472.
[33] Mizuno, N.; Yamaguchi, K.; Matsushita, M. Angew. Chem., Int. Ed. 2004, 43, 1576.
[34] Varma, R. S.; Polshettimar, V. Chem. Eur. J. 2009, 15, 1582.
[35] Kim, A. Y.; Bae, H. S.; Park, S. H; Park, S. K.; Park, R. H. Catal. Lett. 2011, 141, 685.
[36] Shimizu, K. Z.; Imaiida, N.; Sawabe, K.; Satsuma. A. Appl. Catal., A 2012, 421~422, 114.
[37] Tyler, D. R.; Knapp, S. M. M.; Sherbow, T. J.; Yelle, R. B.; Juliette, J. Organometallics 2013, 32, 3744.
[38] Qu, J. P.; Tong, P.; Yang, D. W.; Li, Y.; Wang, B. W. Organometallics 2015, 34, 3571.
[39] Jin, J. Y.; Etzion, R.; Santoso, B.; Yanaranop, P. Polymer 2016, 98, 244.
[40] Alper, H.; Larksarp, C. J. Org. Chem. 2000, 65, 2773.
[41] Inoue, Y.; Tsukada, N.; Ohba, Y. J. Org. Chem. 2003, 687, 436.
[42] Li, Z.; Ding, R. B.; Lu, Z.; Xiao, S. X.; Ma, X. L. J. Mol. Catal. A: Chem. 2006, 250, 100.
[43] Crabtree, R. H.; Hull, J. F.; Hilton, S. T. Inorg. Chim. Acta 2010, 363, 1243.
[44] (a) Giacomelli, G.; Luca, L. D.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272;
(b) Li, Q.; Yan, L. Y.; Xia, D.; Shen, Y. C. Chin. J. Org. Chem. 2011, 31, 2034 (in Chinese).(李倩, 严罗一, 夏定, 申永存, 有机化学, 2011, 31, 2034.)
(c) Dong, D.; Yan, P.; Yu, M. J. Chem. Sci. 2016, 128, 951.
[45] Deng, Y. Q.; Yin, S. F.; Au, C. T. lnd. Eng. Chem. Res. 2012, 51, 9492.
[46] Maronna, M. M.; Kruissink, E. C.; Tinge, J. T.; Agar, D. W.; Hoelderich, W. F. Ind. Eng. Chem. Res. 2016, 55, 1202.
[47] Shin, Y. Y.; Jung, D. J.; Lee, S. G. Catal. 2013, 3, 525.
[48] Mahajan, P. S.; Humne, V. T.; Tanpure, S. D.; Mhaske, S. B. Org. Lett. 2016, 18, 3450.
[49] Zhang, F.-L.; Wang, Y.-F.; Lonca, G. H.; Zhu, X.; Chiba, S. An-gew. Chem., Int. Ed. 2014, 53, 4390.
[50] Zhu, X.; Wang, Y.-F.; Zhang, F.-L.; Chiba, S. Chem. Asian J. 2014, 9, 2458.
[51] Zhang, F. L.; Zhu, X.; Chiba, S. Org. Lett. 2015, 17, 3138.
[52] Howell, A. R.; Chen, D. Tetrahedron Lett. 2015, 56, 3583.
[53] Lüdtke, D. S.; Silva, L.; Affeldt, R. F. J. Org. Chem. 2016, 81, 5464.
[54] Babu, V. V. S.; Vasant, G-R.; Tantry, S. J. Tetrahedron Lett. 2005, 46, 4099.
[55] Li, Z. F.; Lai, G. Q.; Chen, W. F.; Li, K. B.; Hu, Z. Q.; Wang, L. L. Organometallics 2011, 30, 2026.
[56] Liguori, A.; Siciliano, C.; Leggio, A.; Belsito, E. L.; Di, M. L.; Leotta, G. V.; Romio, E. Tetrahedron Lett. 2015, 56, 199.
[57] Gooßen, L. J.; Rauhaus, J. E.; Deng, G. Angew, Chem, Int. Ed. 2005, 44, 4042.
[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.
[59] Takai, K.; Kuninobu, Y.; Salprima, Y. S. Org. Lett. 2007, 9, 5609.
[60] Beller, M.; Fang, X. J.; Jackstell, R. Angew, Chem., Int. Ed. 2013, 52, 14089.
[61] Stephenson, N. A.; Zhu, J.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 10003.
[62] Srinivas, M.; Hudwekar, A. D.; Venkateswalu, V.; Reddy, G. L. Tetrahedron Lett. 2015, 56, 4775.
[63] Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917.
[64] Jin, X. J.; Ka, Z. Y.; Mizuno, N. Chem. Lett. 2012, 41, 866.
[65] Xu, S. X.; Liu, J. Q.; Hu, D. H.; Bi, X. H. Green Chem. 2015, 17, 184.
[66] Huang, H.; Tang, L. N.; Xi, Y.; He, G. K.; Zhu, H. J. Tetrahedron Lett. 2016, 57, 1873.
[67] Ohmura, R.; Takahata, M.; Togo, H. Tetrahedron Lett. 2010, 51, 4378.
[68] Yamaguchi, K.; Kobayashi, H.; Oishi, T.; Mizuno, N. Angew. Chem. 2012, 124, 559.
[69] Wu, A.; Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J. Org. Lett. 2009, 11, 3810.
[70] Peng, Y. Q.; Song, G. H. Org. Prep. Proced. Int. 2002, 34, 95.
[71] Ahmed, M.; Baburajan, P.; Sureshm, A. S. Tetrahedron Lett. 2015, 56, 4864.
[72] Wang, Y.; Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2012, 51, 7250.
[73] Wang, T.; Yuan, L.; Zhao, Z.; Shao, A.; Gao, M.; Huang, Y.; Xiong, F.; Zhang, H.; Zhao, J. Green Chem. 2015, 17, 2741.
[74] Zhao, J.; Zhao, Z.; Wang, T.; Yuan, L.; Hu, X.; Xiong, F. Adv. Synth. Catal. 2015, 357, 2566.
[75] Griffin, J. M.; Atherton, J. H.; Page, M. I.; Powles, N. T. J. Phys. Org. Chem. 2016, 29, 768.
[76] Batra, S.; Dighe, S. U. Adv. Synth. Catal. 2016, 358, 500.

Outlines

/

〈 〉