酰胺类化合物合成的最新研究进展

doi:10.6023/cjoc201608014

摘要/Abstract

酰胺键的形成是有机化学中最重要的反应之一.因为酰胺类广泛存在于现代药物和生物活性物质中，然而酰胺键的合成作为当代的挑战经常被忽视.目前存在的方法有着它们固有的局限性，避免浪费和降低成本越来越受到人们的重视，开发新颖的形成酰胺键的化学方法势在必行.在合成酰胺键的许多方法中，利用催化方法来制备这类重要的官能团备受人们关注.催化剂用于形成酰胺键已成为在关键领域中一些最新文献的亮点.醇、醛、酮、不饱烃等作为底物和有机胺或无机胺在各种条件下反应得到相应的酰胺.回顾并总结酰胺的合成方法有助于解决目前工艺中存有的问题.

关键词: 酰胺, 催化剂, 有机胺, 氨水

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.

Key words: amides, catalyst, organic amine, ammonia

引用此文

董浩, 侯梅芳. 酰胺类化合物合成的最新研究进展[J]. 有机化学, 2017, 37(2): 267-283.

Dong Hao, Hou Meifang. Recent Progress in Synthesis of Amides[J]. Chin. J. Org. Chem., 2017, 37(2): 267-283.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[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.