Chinese Journal of Organic Chemistry >
Progress in Oxidative Coupling of Amines to Imines
Received date: 2018-01-09
Revised date: 2018-02-09
Online published: 2018-02-11
Supported by
Project supported by the Open Foundation of the State Key Laboratory of Bioactive Seaweed Substances (No. SKL-BASS1723).
Imines are a class of active intermediates and have good antibacterial activity, therefore, they have received the extensive concern of scientists. Since the preparation method of imines by oxidative coupling of amines has the advantages of high atom economy and environmental friendliness, it has become a research hotspot. The recent progress in oxidative coupling of amines to imines is summarized from two aspects:catalyst and catalytic mechanism in this article. We introduced all kinds of catalytic systems in detail such as noble metal, non-noble metal, photocatalysis, biomimetic catalysis, poly aniline, graphite oxide, and azobisisobutyronitrile (AIBN). The catalytic performance, advantages and drawbacks and applicability of which are highlighted. And the catalytic mechanisms of the main catalytic systems are also discussed. It should be pointed out that these catalytic systems for oxidative coupling of amines to imines showed varying degrees of success as well as limitations like high cost of catalyst, harsh reaction condition, use of oxidant, alkaline additives and/or toxic organic solvents. Finally, based on the existential problems for oxidative coupling of amines to imines, the research directions in this field are predicted.
Liu Di , Zhang Chenghui , Han Nan , Du Mengmeng , Zhang Xiaolu , Zhao Pengshan , Yang Ping . Progress in Oxidative Coupling of Amines to Imines[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1350 -1363 . DOI: 10.6023/cjoc201801017
[1] Kobayashi, S.; Mori, Y.; Fossey, J.-S.; Salter, M.-M. Chem.Rev. 2011, 111, 2626.
[2] Adams, J.-P. J.Chem. Soc., Perkin Trans.1 2000, 125.
[3] Ashok, M.; Holla, B.-S.; Poojary, B. Eur.J.Med.Chem. 2007, 46, 1095.
[4] Young, J.-N.; Chang, T.-C.; Tsai, S.-C.; Yang, L.; Yu, S.-C. J.Catal. 2010, 272, 253.
[5] Santos, L.-L.; Serna, P.; Corma, A. Chem.-Eur.J. 2009, 15, 8196.
[6] Zanardi, A.; Mata, J.-A.; Peris, E. Chem.-Eur.J. 2010, 16, 10502.
[7] Maggi, A.; Madsen, R. Organometallics 2012, 31, 451.
[8] Kwon, M.-S.; Kim, S.; Park, S.; BoscoO, W.; Chidrala, R.-K.; Park, J. J.Org.Chem. 2009, 74, 2877.
[9] Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org.Lett. 2009, 11, 4568.
[10] Bailey, A.-J.; James, B.-R. Chem.Commun. 1996, 0, 2343.
[11] Prades, A.; Peris, E.; Albrecht, M. Organometallics 2011, 30, 1162.
[12] Doctorovich, F.; Granara, M.; Salvo, F.-D. Transition Met. Chem. 2001, 26, 505.
[13] He, L.-P.; Chen, T.; Gong, D.; Lai, Z.; Huang, K.-W. Organometallics 2012, 31, 5208.
[14] Zhang, Y.-C.; Lu, F.; Huang, R.; Zhang, H.-Y.; Zhao, J.-Q. Catal.Commun. 2016, 81, 10.
[15] Zhu, B.; Angelici, R.-J. Chem.Commun. 2007, 38, 2157.
[16] Zhu, B.; Lazar, M.; Trewyn, B.-G.; Angelici, R.-J. J.Catal. 2008, 260, 1.
[17] Grirrane, A.; Corma, A.; Garcia, H. J.Catal. 2009, 264, 138.
[18] Perez, Y.; Aprile, C.; Corma, A.; Garcia, H. Catal Lett. 2010, 134, 204.
[19] Ishida, T.; Kawakita, N.; Akita, T.; Haruta, M. Gold Bull. 2009, 42, 267.
[20] Srimani, D.; Feller, M.; Ben-David, Y.; Milstein, D. Chem.Commun. 2012, 48, 11853.
[21] Lu, S.-L.; Wang, J. Q.; Cao, X. Q.; Li, X. M.; Gu, H. W. Chem. Commun. 2014, 50, 3512.
[22] Patil, R.-D.; Adimurthy, S. Adv.Synth. Catal. 2011, 353, 1695.
[23] Patil, R.-D, Adimurthy, S. RSC Adv. 2012, 2, 5119.
[24] Patil, R.-D, Adimurthy, S. Asian J.Org. Chem. 2013, 2, 726.
[25] Hu, Z.-Z.; Kerton, F.-M. Org.Biomol.Chem. 2012, 10, 1618.
[26] Huang, B.; Tian, H.; Lin, S.; Xie, M.; Yu, X.; Xu, Q. Tetrahedron Lett. 2013, 54, 2861.
[27] Largeron, M.; Fleury, M.-B. Chem.-Eur. J. 2015, 21, 1.
[28] Wang, J.; Lu, S.; Cao, X.; Gu, H. Chem.Commun. 2014, 50, 5637.
[29] Al-Hmoud, L.; Jones, C.-W. J.Catal. 2013, 301, 116.
[30] Marui, K.; Nomoto, A.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2015, 56, 1200.
[31] Chu, G.-B.; Li, C.-B. Org.Biomol. Chem. 2010, 8, 4716.
[32] Wang, L.-Y.; Chen, B.; Ren, L.-H.; Zhang, H.-Y.; Lü, Y.; Gao, S. Chin.J.Catal. 2015, 36, 19.
[33] Kodama, S.; Yoshida, J.; Nomoto, A.; Ueta, Y.; Yano, S.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2010, 41, 2450.
[34] Neumann, R.; Levin, M.-J. J.Org.Chem. 1991, 56, 5707.
[35] Nakayama, K.; Hamamoto, M.; Nishiyama, Y.; Ishii, Y. Chem.Lett. 1993, 22, 1699.
[36] Reddy, J.-S.; Sayari, A. Catal.Lett. 1994, 28, 263.
[37] Maruyama, K.; Kusukawa, T.; Highchi, Y.; Nishinaga, A. Chem.Lett. 1991, 7, 1093.
[38] Zhao, S.; Liu, C.; Guo, Y.; Xiao, J.-C.; Chen, Q.-Y. J.Org. Chem. 2014, 79, 8926.
[39] Zhang, C.-H.; Zhao, P.-S.; Zhang, Z.-L.; Zhang, J.-W.; Yang, P.; Gao, P.; Gao, J.; Liu, D. RSC Adv. 2017, 7, 47366.
[40] Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. ChemCatChem 2010, 2, 1438.
[41] Zhang, E.; Tian, H.-W.; Xu, S.-D.; Yu, X.-C.; Xu, Q. Org.Lett. 2013, 15, 2704.
[42] Gopalaiah, K.; Saini, A. Catal.Lett. 2016, 146, 1648.
[43] Kim, S.-S.; Thakur, S.-S.; Song, J.-Y.; Lee, K.-H. Bull.Korean Chem.Soc. 2005, 26, 499.
[44] Choudary, B.-M.; Narender, N.; Bhuma, V. Synth.Commun. 1996, 26, 631.
[45] Ohtani, B.; Osaki, H.; Nishimoto, S.-I.; Kagia, T. Chem.Lett. 1985, 21, 1075.
[46] Lang, X.; Ji, H.; Chen, C.; Ma, W.; Zhao, J. Angew.Chem., Int.End. 2011, 50, 3934.
[47] Lang, X.; Ma, W.; Zhao, Y.; Chen, C.; Ji, H.; Zhao, J. Chem.-Eur. J. 2012, 18, 2624.
[48] Li, N.; Lang, X.-J.; Ma, W.-H.; Ji, H.-W.; Chen, C.-C.; Zhao, J.-C. Chem. Commun. 2013, 49, 5034.
[49] Bu, J.; Fang, J.; Leow, W.-R.; Zheng, K.-H.; Chen, X.-D. RSC Adv. 2015, 5, 103895.
[50] Dai, J.; Yang, J.; Wang, X.-H.; Zhang, L.; Li, Y. Appl.Surf.Sci. 2015, 349, 343.
[51] Zavahir, S.; Zhu, H. Molecules 2015, 20, 1941.
[52] Furukawa, S.; Ohno, Y.; Shishido, T.; Teramura, K.; Tanaka, T. ACS Catal. 2011, 1, 1150.
[53] Su, F.; Mathew, S.-C.; Möhlmann, L.; Antonietti, M.; Wang, X.; Blechert, S. Angew.Chem., Int.Ed. 2011, 50, 657.
[54] Park, J.-H.; Ko, K.-C.; Kim, E.; Park, N.; Ko, J.-H.; Ryu, D.-H.; Ahn, T.-K.; Lee, J.-Y.; Son, S.-U. Org. Lett. 2012, 14, 5502.
[55] Jin, J.; Shin, H.-W.; Park, J.-H.; Park, J.-H.; Kim, E.; Ahn, T.-K.; Ryu, D.-H.; Son, S.-U. Organometallics 2013, 32, 3954.
[56] Berlicka, A.; König, B. Photochem.Photobiol.Sci. 2010, 9, 1359.
[57] Naya, S.-I.; Kimura, K.; Tada, H. ACS Catal. 2013, 3, 10.
[58] Ye, L.; Li, Z.-H. ChemCatChem 2014, 6, 2540.
[59] Mure, M.; Klinman, J.-P. J.Am.Chem.Soc. 1995, 117, 8698.
[60] Mure, M.; Klinman, J.-P. J.Am.Chem. Soc. 1995, 117, 8707.
[61] Lee, Y.; Sayre, L.-M. J.Am.Chem.Soc. 1995, 117, 11823.
[62] Ling, K.-Q.; Kim, J.; Sayre, L.-M. J.Am.Chem. Soc. 2001, 123, 9606.
[63] Wendlandt, A.-E.; Stahl, S.-S. Org.Lett. 2012, 14, 2850.
[64] Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J.Am. Chem.Soc. 2012, 134, 13970.
[65] Yuan, Q.-L.; Zhou, X.-T.; Ji, H.-B. Catal. Commun. 2010, 12, 202.
[66] Tollari, S.; Fumagalli, A.; Porta, F. Inorg.Chim.Acta 1997, 247, 71.
[67] Kim, S.-S.; Thakur, S.-S.; Bull, K. Chem.Soc. 2005, 26, 1600.
[68] Zhou, X.-T.; Ren, Q.-G.; Ji, H.-B. Tetrahedron Lett. 2012, 53, 3369.
[69] Higuchi, M.; Ikeda, I.; Hirao, T. J.Org.Chem. 1997, 62, 1072.
[70] Huang, H.; Huang, J.; Liu, Y.-M.; He, H.-Y.; Cao, Y.; Fan, K.-N. Green Chem. 2012, 14, 930.
[71] Landge, S.-M.; Atanassova, V.; Thimmaiah, M.; Török, B. Tetrahedron Lett. 2007, 48, 5161.
[72] Liu, L.; Wang, Z.; Fu, X.; Yan, C.-H. Org. Lett. 2012, 14, 5692.
/
| 〈 |
|
〉 |