氯化亚铁催化的醛与伯胺和仲胺的氧化酰胺化反应
收稿日期: 2015-04-27
网络出版日期: 2015-06-15
基金资助
项目受中国人民大学科学研究基金(中央高校基本科研业务费专项资金资助)项目成果(No.10XNL017)资助.
FeCl2-Catalyzed Oxidative Amidation of Aldehydes with Primary and Secondary Amines
Received date: 2015-04-27
Online published: 2015-06-15
Supported by
Project supported by the Fundamental Research Funds for the Central Universities and the Research Funds of Renmin University of China(No. 10XNL017).
李远明 , 贾凡 , 马丽娜 , 李志平 . 氯化亚铁催化的醛与伯胺和仲胺的氧化酰胺化反应[J]. 化学学报, 2015 , 73(12) : 1311 -1314 . DOI: 10.6023/A15040287
The amidation reaction is an important process in both academia and industry for the synthesis of natural products, functional polymers, and pharmaceuticals. The development of new amidation methods for constructing such important class of organic compounds is still attracting considerable interests. We herein reported a general oxidative amidation of aldehydes with a variety of free primary or secondary amines using inexpensive iron(II) chloride as catalyst and tert-butyl hydroperoxide(TBHP) as oxidant. The present amidation reactions afford the corresponding secondary and tertiary amides in moderate to excellent yields. In addition, the amidations of benzimidazole and pyrazole were also achieved by the developed method.
Key words： iron catalysis; oxidative; amidation; aldehyde; amine
[1] (a) Li, L.; Zhou, B.; Ye, L. Chin. J. Org. Chem. 2015, 35, 655.(李龙, 周波, 叶龙武, 有机化学, 2015, 35, 655.);
(b) Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471;
(c) Allen, C. L.; Williams, J. M. J. Chem. Soc. Rev. 2011, 40, 3405.
[2] (a) Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606;
(b) Montalbetti, C. A. G. N.; Falque, V. Tetrahedron 2005, 61, 10827.
[3] Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146.
[4] (a) Qin, C.; Zhou, W.; Chen, F.; Ou, Y.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 12595;
(b) Li, Q.; Yan, L.; Xia, D.; Shen, Y. Chin. J. Org. Chem. 2011, 31, 2034.(李倩, 严罗一, 夏定, 申永存, 有机化学, 2011, 31, 2034.);
(c) Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 3599;
(d) Mao, D.; Lu, G.; Chen, Q.; Xie, Z.; Zhang, Y. Acta Chim. Sinica 2001, 59, 1139.(毛东森, 卢冠忠, 陈庆龄, 谢在库, 张玉贤, 化学学报, 2001, 59, 1139.)
[5] (a) Köhn, M.; Breinbauer, R. Angew. Chem. Int. Ed. 2004, 43, 3106;
(b) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408;
(c) Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007.
[6] (a) Chen, J.; Mao, J.; Zheng, Y. Chin. J. Org. Chem. 2015, 35, 672.(陈洁, 毛金成, 郑洋, 有机化学, 2015, 35, 672.);
(b) Wang, H.; Yang, L.; Xiao, Y.; Mao, P.; Zhu, X.; Yuan, J.; Qu, L. Chin. J. Org. Chem. 2014, 34, 355.(王宏雁, 杨亮茹, 肖咏梅, 毛璞, 朱晓亮, 袁金伟, 屈凌波, 有机化学, 2014, 34, 355.);
(c) Martinelli, J. R.; Clark, T. P.; Watson, D. A.; Munday, R. H.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 8460;
(d) Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046.
[7] (a) Ding, Y.; Zhang, X.; Zhang, D.; Chen, Y.; Wu, Z.; Wang, P.; Xue, W.; Song, B.; Yang, S. Tetrahedron Lett. 2015, 56, 831;
(b) Ghosh, S. C.; Ngiam, J. S. Y.; Chai, C. L. L.; Seayad, A. M.; Dang, T. T.; Chen, A. Adv. Synth. Catal. 2012, 354, 1407;
(c) Ekoue-Kovi, K.; Wolf, C. Chem. Eur. J. 2008, 14, 6302.
[8] Markó, I. E.; Mekhalfia, A. Tetrahedron Lett. 1990, 31, 7237.
[9] Gilman, N. W. J. Chem. Soc. D 1971, 733.
[10] Shie, J.-J.; Fang, J.-M. J. Org. Chem. 2003, 68, 1158.
[11] (a) De Sarkar, S.; Studer, A. Org. Lett. 2010, 12, 1992;
(b) Vora, H. U.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 13796;
(c) Tan, B.; Toda, N.; Barbas, C. F. Angew. Chem., Int. Ed. 2012, 51, 12538;
(d) Yao, H.; Tang, Y.; Yamamoto, K. Tetrahedron Lett. 2012, 53, 5094;
(e) Ji, M.; Lim, S.; Jang, H.-Y. RSC Adv. 2014, 4, 28225.
[12] (a) Vanjari, R.; Guntreddi, T.; Singh, K. N. Green Chem. 2014, 16, 351;
(b) Cadoni, R.; Porcheddu, A.; Giacomelli, G.; De Luca, L. Org. Lett. 2012, 14, 5014;
(c) Porcheddu, A.; Luca, L. D. Adv. Synth. Catal. 2012, 354, 2949.
[13] (a) Wang, J.; Li, J.; Xu, F.; Shen, Q. Adv. Synth. Catal. 2009, 351, 1363;
(b) Seo, S.; Marks, T. J. Org. Lett. 2008, 10, 317;
(c) Seo, S.; Marks, T. J. Org. Lett. 2007, 10, 317;
(d) Li, J.; Xu, F.; Zhang, Y.; Shen, Q. J. Org. Chem. 2009, 74, 2575.
[14] Tamaru, Y.; Yamada, Y.; Yoshida, Z. Synthesis 1983, 474.
[15] Ekoue-Kovi, K.; Wolf, C. Org. Lett. 2007, 9, 3429.
[16] (a) Dai, W.; Liu, Y.; Tong, T.; Li, X.; Luo, F. Chin. J. Catal. 2014, 35, 1012;
(b) Tillack, A.; Rudloff, I.; Beller, M. Eur. J. Org. Chem. 2001, 2001, 523.
[17] (a) Yoo, W.-J.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 13064;
(b) Ghosh, S. C.; Ngiam, J. S. Y.; Seayad, A. M.; Tuan, D. T.; Chai, C. L. L.; Chen, A. J. Org. Chem. 2012, 77, 8007;
(c) Suresh Kumar, A.; Thulasiram, B.; Bala Laxmi, S.; Rawat, V. S.; Sreedhar, B. Tetrahedron 2014, 70, 6059.
[18] Ghosh, S. C.; Ngiam, J. S. Y.; Chai, C. L. L.; Seayad, A. M.; Dang, T. T.; Chen, A. Adv. Synth. Catal. 2012, 354, 1407.
[19] Zhang, M.; Wu, X.-F. Tetrahedron Lett. 2013, 54, 1059.
[20] (a) Jia, F.; Li, Z. Org. Chem. Front. 2014, 1, 194;
(b) Li, Y.; Jia, F.; Li, Z. Chem. Eur. J. 2013, 19, 82;
(c) Li, Y.; Ma, L.; Jia, F.; Li, Z. J. Org. Chem. 2013, 78, 5638;
(d) Li, Y.; Ma, L.; Li, Z. Chin. J. Org. Chem. 2013, 33, 704.(李远明, 马丽娜, 李志平, 有机化学, 2013, 33, 704.);
(e) Ma, L.; Li, Y.; Li, Z. Sci. China Chem. 2015, 58, 1310.
[21] (a) Leung, C. H.; Voutchkova, A. M.; Crabtree, R. H.; Balcells, D.; Eisenstein, O. Green Chem. 2007, 9, 976;
(b) Gao, J.; Wang, G.-W. J. Org. Chem. 2008, 73, 2955.
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