Recent Advances and Applications in N-Methylation of Amines and Imines

doi:10.6023/cjoc201912031

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1874-1890.DOI: 10.6023/cjoc201912031 Previous Articles Next Articles

胺和亚胺氮甲基化反应的研究进展

严沣^a,b, 蔡爽^a,b, 闻武^a,b, 文蔚^a,b, 李博解^a, 汪连生^a, 朱磊^a,c

a 湖北工程学院化学与材料科学学院湖北孝感 432000;
b 湖北大学材料科学与工程学院武汉 430062;
c 华中科技大学生物无机化学与药物湖北省重点实验室武汉 430074

收稿日期:2019-12-22 修回日期:2020-04-05 发布日期:2020-04-17
通讯作者: 李博解, 汪连生, 朱磊 E-mail:bojie.li@hbeu.edu.cn;wangls@hbeu.edu.cn;lei.zhu@hbeu.edu.cn
基金资助:
国家自然科学基金（No.21774029）、湖北省高等学校优秀中青年科技创新团队计划（No.T201816）、湖北省自然科学基金（No.2019CFB354）、生物无机化学与药物湖北省重点实验室开放基金（No.BCMM201805）、孝感市自然科学计划（No.XGKJ201910047）、湖北省“楚天学者”计划（朱磊）和湖北工程学院高水平硕士学位论文培育资助项目.

Recent Advances and Applications in N-Methylation of Amines and Imines

Yan Feng^a,b, Cai Shuang^a,b, Wen Wu^a,b, Wen Wei^a,b, Li Bojie^a, Wang Liansheng^a, Zhu Lei^a,c

a School of Chemistry and Materials Science, Hubei Engineering University, Xiaogan, Hubei 432000;
b School of Materials Science and Engineering, Hubei University, Wuhan 430062;
c Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, Huazhong University of Science and Technology, Wuhan 430074

Received:2019-12-22 Revised:2020-04-05 Published:2020-04-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21774029), the Hubei University Excellent Young and Middle-Aged Science and Technology Innovation Team Project (No. T201816), the Opening Fund of Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica (No. BCMM201805), the Natural Science Foundation of Xiaogan City (No. XGKJ201910047), the "Chutian Scholar" Program of Hubei Province (Lei Zhu), and the High-Level Master's Thesis Cultivation Project of Hubei Engineering University.

N-Methylation of amines and imines is one of the most important reactions for C-N bond formation. It is widely utilized for both laboratary research and industrial applications. Traditional methylation reactions involve the use of flammable, explosive and toxic starting materials. In contrast, newly developed methods have overcome this point and provide a mild strategy. In this transformation, C1 carbon source for the methyl group is important which determines the type of catalyst, reaction conditions and substrate scope. Herein, the research progress for the N-methylation of amines and imines is summarized based on different C1 carbon source.

Key words: N-methylation, carbon dioxide, formic acid, methanol, metal catalyst

Cite this article

Yan Feng, Cai Shuang, Wen Wu, Wen Wei, Li Bojie, Wang Liansheng, Zhu Lei. Recent Advances and Applications in N-Methylation of Amines and Imines[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1874-1890.

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[1] Bissember, A. C.; Lundgren, R. J.; Creutz, S. E.; Peters, J. C.; Fu, J. C. Angew. Chem., Int. Ed. 2013, 52, 5129.
[2] Cho, S. H.; Kim, J. Y.; Lee, S. Y.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 9127.
[3] Tanaka, R.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14168.
[4] Jacquet, O., Gomes, C. D. N., Ephritikhine, M.; Cantat, T. J. Am. Chem. Soc. 2012, 134, 2934.
[5] Arakara, H.; Aresta, M.; Armor, J. N.; Barteau, M. A.; Beckman, E. J.; Bell, A. T.; Bercaw, J. E.; Creutz, C.; Dinjus, E.; Dixon, D. A.; Domen, K.; DuBois, D. L.; Eckert, J.; Fujita, E.; Gibson, D. H.; Goddard, W. A.; Goodman, D. W.; Keller, J.; Kubas, G. J.; Kung, H. H.; Lyons, J. E.; Manzer^·, L. E.; Marks, T. J.; Morokuma, K.; Nicholas, K. M.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W. M. H.; Schmidt, L. D.; Sen, A.; Somorjai, G. A.; Stair, P. C.; Stults, B. R.; Tumas, W. Chem. Rev. 2001, 101, 953.
[6] Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
[7] Wang, W.; Wang, S.-P.; Ma, X.-B.; Gong, J.-L. Chem. Soc. Rev. 2011, 40, 3703.
[8] Fernández-Alvarez, F. J.; Aitani, A. M.; Oro, L. A. Catal. Sci. Technol. 2014, 4, 611.
[9] Gomes, C. D. N.; Jacquet, O.; Villiers, C.; Thuéry, P.; Ephritikhine, M.; Cantat, T. Angew. Chem., Int. Ed. 2012, 51, 187.
[10] Khandelwal, M.; Wehmschulte, R. J. Angew. Chem., Int. Ed. 2012, 51, 7323.
[11] Jacquet, O.; Gomes, C. D. N.; Ephritikhine, M.; Cantat, T. ChemCatChem 2013, 5, 117.
[12] Li, Y.; Fang, X.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 9568.
[13] Tlili, A.; Frogneux, X.; Blondiaux, E.; Cantat, T. Angew. Chem., Int. Ed. 2014, 53, 2543.
[14] Li, Y.; Sorribes, I.; Yan, T.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 12156.
[15] Jacquet, O.; Frognuex, X.; Gomes, C. D. N.; Cantat, T. Chem. Sci. 2013, 4, 2127.
[16] Blondiaux, E.; Pouessel, J.; Cantat, T. Angew. Chem., Int. Ed. 2014, 53, 12186.
[17] Beydoun, K.; Stein, T. v.; Klankermayer, J.; Lertner, W. Angew. Chem., Int. Ed. 2013, 52, 9554.
[18] Beydoun, K.; Ghattas, G.; Thenert, K.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2014, 53, 11010.
[19] Cui, X.; Dai, X.; Zhang, Y.; Deng, Y.; Shi, F. Chem. Sci. 2014, 5, 649.
[20] Cui, X.; Zhang, Y.; Deng, Y.; Shi, F. Chem. Commun. 2014, 50, 13521.
[21] Kon, K.; Siddiki, S. M. A. H.; Onodera, W.; Shimizu, K. Chem.- Eur. J. 2014, 20, 6264.
[22] Yang, Z.; Yu, B.; Zhang, H.; Zhao, Y.; Ji, G.; Ma, Z.; Gao, X.; Liu, Z. Green Chem. 2015, 17, 4189.
[23] Yang, Z.; Yu, B.; Zhang, H.; Zhao, Y.; Ji, G.; Liu, Z. RSC Adv. 2015, 5, 19613.
[24] Yang, Z.; Yu, B.; Zhang, H.; Zhao, Y.; Yu, C.; Ma, Z.; Ji, G.; Gao, X.; Han, B.; Liu, Z. ACS Catal. 2016, 6, 1268.
[25] Liger, F.; Eijsbout, T.; Cadarossanesaib, F.; Tourvieille, C.; Bars, D. L.; Billard, T. Eur. J. Org. Chem. 2015, 6434.
[26] Du, X.-L.; Tang, G.; Bao, H.-L.; Jiang, Z.; Zhong, X.-H.; Su, D. S.; Wang, J.-Q. ChemSusChem 2015, 8, 3489.
[27] Lucero, G.-S; Marcos, F.-A; Juventino, J. G. Organometallics 2015, 34, 763.
[28] Santoro, O.; Lazreg, F.; Minenkov, Y.; Cavallo, L.; Cazin, C. S. J. Dalton. Trans. 2015, 44, 18138.
[29] Chen, W.-C.; Shen, J.-S.; Jurca, T.; Peng, C.-J.; Lin, Y.-H.; Wang, Y.-P.; Shih, W.-C.; Yap, G. P. A.; Ong, T.-G. Angew. Chem., Int. Ed. 2015, 54, 15422.
[30] Nguyen, T. V. Q.; Yoo, W.-J.; Kobayashi, S. Adv. Synth. Catal. 2016, 358, 452.
[31] Liu, X.-F.; Li, X.-Y.; Qiao, C.; Fu, H.-C.; He, L.-N. Angew. Chem., Int. Ed. 2017, 56, 7425.
[32] Li, G.; Chen, J.; Zhu, D.-Y.; Chen, Y.; Xia, J.-B. Adv. Synth. Catal. 2018, 360, 2364.
[33] Sorribes, I.; Junge, K.; Beller, M. Chem.-Eur. J. 2014, 20, 7878.
[34] Savourey, S.; Lefèvre, G.; Berthet, J.-C.; Cantat, T. Chem. Commun. 2014, 50, 14033.
[35] Fu, M.-S.; Shang, R.; Cheng, W.-M.; Fu, Y. Angew. Chem., Int. Ed. 2015, 54, 9042.
[36] Zhu, L.; Li, B.-J.; Wang, S.; Wang, W.; Wang, L.-S.; Ding, L.; Qin, C.-Q. Polymers 2018, 10, 385.
[37] Wen, W.; Han, B.; Yan, F.; Ding, L.; Li, B.-J.; Wang, L.-S.; Zhu, L. Nanomaterials 2018, 8, 326.
[38] Zhu, L.; Wang, L.-S.; Li, B.-J.; Li. W.; Fu. B.-Q. Catal. Sci. Technol. 2016, 6, 6172.
[39] Andrew, K. G.; Summers, D. M.; Donnelly, L. J.; Denton, R. M. Chem. Commun. 2016, 52, 1855.
[40] Qiao, C.; Liu, X.-F.; Liu, X.; He, L.-N. Org. Lett. 2017, 19, 1490.
[41] Natte, K.; Neumann, H.; Beller, M.; Jagadeesh, R. V. Angew. Chem., Int. Ed. 2017, 56, 6384.
[42] Chen, Y. Chem.-Eur. J. 2019, 25, 3405.
[43] Dominguez-Huerta A.; Dai X.-J.; Zhou, F.; Querard, P.; Qiu, Z.; Ung, S.; Liu, W.; Li, J.-B.; Li, C.-J. Can. J. Chem. 2019, 97, 67.
[44] Xu, C.-P.; Xiao, Z.-H.; Zhuo, B.-Q.; Wang, Y.-H.; Huang, P.-Q. Chem. Commun. 2010, 46, 7834.
[45] Yan, T.; Feringa, B. L.; Barta, K. Sci. Adv. 2017, 3, eaao6494.
[46] Zhang, L.; Zhang, Y.; Deng, Y.; Shi, F. RSC. Adv. 2015, 5, 14514.
[47] Tsarev, V. N.; Morioka, Y.; Caner, J.; Wang, Q.; Ushimaru, R.; Kudo, A.; Naka, H.; Saito, S. Org. Lett. 2015, 17, 2530.
[48] Dang, T. T.; Ramalingam, B.; Seayad, A. M. ACS Catal. 2015, 5, 4082.
[49] Campos, J.; Sharninghausen, L. S.; Manas, M. G.; Crabtree, R. H. Inorg. Chem. 2015, 54, 5079.
[50] Elangovan, S.; Neumann, J.; Sortais, J.-B.; Junge, K.; Darcel, C.; Beller, M. Nat. Commun. 2016, 7, 12641.
[51] Bruneau-Voisine, A.; Wang, D.; Dorcet, V.; Roisnel, T.; Darcel, C.; Sortais, J.-B. J. Catal. 2017, 347, 57.
[52] Liu, Z.; Yang, Z.; Yu, X.; Zhang, H.; Yu, B.; Zhao, Y.; Liu, Z. Adv. Synth. Catal. 2017, 359, 4278.
[53] Goyal, V.; Gahtori, J.; Narani, A.; Gupta, P.; Bordoloi, A.; Natte, K. J. Org. Chem. 2019, 84, 15389.
[54] Liang, R.; Li, S.; Wang, R.; Lu, L.; Li, F. Org. Lett. 2017, 19, 5790.
[55] Zhu, L.; Wang, L.-S.; Li, B.-J.; Fu, B.-Q.; Zhang, C.-Q.; Li, W. Chem. Commun. 2016, 52, 6371.
[56] Jiang, X.; Wang, C.; Wei, Y.; Xue, D.; Liu, Z.; Xiao, J. Chem.-Eur. J. 2014, 20, 58.
[57] Wang, H.; Huang, Y.; Dai, X.; Shi, F. Chem. Commun. 2017, 53, 5542.
[58] Ge, X.; Luo, C.; Qian, C.; Yu, Z.; Chen, X. RSC Adv. 2014, 4, 43195.
[59] Li, Y.; Sorribes, I.; Vicent, C.; Junge, K.; Beller, M. Chem.-Eur. J. 2015, 21, 16759.

胺和亚胺氮甲基化反应的研究进展

Recent Advances and Applications in N-Methylation of Amines and Imines

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