SIOC English
有机化学
高级检索

有机化学 >

2019 , Vol. 39 >Issue 2: 475 - 481

DOI: https://doi.org/10.6023/cjoc201808013

研究论文

钯催化的肉桂基碳酸酯化合物与酰腙的烯丙基胺化反应

  • 刘澜涛 ,
  • 陈莹莹 ,
  • 张安安 ,
  • 刘雪 ,
  • 张丽 ,
  • 白静茹 ,
  • 李恒 ,
  • 毛国梁
展开
  • a 商丘师范学院化学化工学院 商丘 476000;
    b 东北石油大学化学化工学院 大庆 163318;
    c 郑州大学化学与分子工程学院 郑州 450001

收稿日期: 2018-08-13

  修回日期: 2018-09-03

  网络出版日期: 2018-09-10

基金资助

国家自然科学基金（No.21572126）、河南省高校科技创新人才基金（No.14HASTIT016）和河南省科技创新杰出人才（No.2018JQ0011）资助项目.

收起

Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones

  • Liu Lantao ,
  • Chen Yingyinga ,
  • Zhang An'an ,
  • Liu Xue ,
  • Zhang Li ,
  • Bai Jingru ,
  • Li Heng ,
  • Mao Guoliang
Expand
  • a College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000;
    b College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318;
    c College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received date: 2018-08-13

  Revised date: 2018-09-03

  Online published: 2018-09-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011).

Fold

摘要

烯丙基胺结构单元广泛存在于天然产物、药物和功能材料分子中，另外烯丙基胺衍生物也是一类重要的有机合成子.实现了钯催化的肉桂基碳酸酯化合物和酰腙化合物的烯丙基胺化反应，高选择性地生成了线型烯丙基胺类化合物，产率高达99%.该方法具有不需要加碱、条件温和、操作简单、底物适应范围广等优点.

关键词： 钯催化剂; 烯丙基胺化反应; 肉桂基碳酸酯

本文引用格式

刘澜涛 , 陈莹莹 , 张安安 , 刘雪 , 张丽 , 白静茹 , 李恒 , 毛国梁 . 钯催化的肉桂基碳酸酯化合物与酰腙的烯丙基胺化反应[J]. 有机化学, 2019 , 39(2) : 475 -481 . DOI: 10.6023/cjoc201808013

Abstract

Allylic amines moiety exists extensively in natural products, medicines and functional materials. In addition, they are also a kind of versatile building blocks for organic synthesis. Using CH3CN as solvent, the palladium catalyzed allyl amination of cinnamyl carbonate and acylhydrazone compounds was realized under argon. The linear product was formed selectively and the up to 99% yield was obtained. The reaction has features of base free, mild reaction condition, simple operation and broad substrate scope.

Key words： paladium catalysis; allylic amination; cinnamyl carbonate

参考文献

[1] (a) Brown, E. G. Ring Nitrogen and Key Biomolecules, Springer, Boston, MA, 1998.
(b) Yu, X. Y.; Zhou, F.; Chen, J. R.; Xiao, W. J. Acta Chim. Sinica 2017, 75, 86(in Chinese). (余晓叶, 周帆, 陈加荣, 肖文精, 化学学报, 2017, 75, 86.)
(c) Li, W. F.; Ma, Q.; Zheng, Z. Z.; Zhang, Y. G. Acta Chim. Sinica 2017, 75, 225(in Chinese). (李宛飞, 马倩, 郑召召, 张跃钢, 化学学报, 2017, 75, 225.)
(d) Li, T. T.; Zhao, J. K.; Li, R.; Quan, Z. L.; Xu, J. Acta Chim. Sinica 2017, 75, 485(in Chinese). (李甜甜, 赵继宽, 李尧, 全贞兰, 徐洁, 化学学报, 2017, 75, 485.)
[2] (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
(b) Trost, B. M.; Pissot-Soldermann, C.; Chen, I.; Schroede, G. M. J. Am. Chem. Soc. 2004, 126, 4480.
(c) Wang, D.; Yu, X.; Ge, B.; Miao, H.; Ding, Y. Chin. J. Org. Chem. 2015, 35, 676(in Chinese). (王大伟, 余晓丽, 葛冰洋, 苗红艳, 丁玉强, 有机化学, 2015, 35, 676.)
(d) Hu, X.; Yang, B.; Yao, W.; Wang, D. Chin. J. Org. Chem. 2018, 38, 3296(in Chinese). (胡欣宇, 杨伯斌, 姚玮, 王大伟, 有机化学, 2018, 38, 3296.)
[3] (a) Monk, J. P.; Brogden, R. N. Drugs 1991, 42, 659.
(b) Birnbaum, J. E. J. Am. Acad. Dermatol. 1990, 23, 782.
(c) Xu, Z.; Wang, D. S.; Yu, X.; Yang Y.; Wang, D. Adv. Synth. Catal. 2017, 359, 3332.
[4] (a) Stuetz, A.; Petranyi, G. J. Med. Chem. 1984, 27, 1539.
(b) Rudisill, D. E.; Castonguay, L. A.; Me, J. K. Tetrahedron Lett. 1988, 29, 1509.
(c) Balfour, J. A.; Fauids, D. Drugs 1992, 43, 259.
(d) Ge, C.; Sang, X.; Yao, W.; Zhang L.; Wang, D. Green Chem. 2018, 20, 1805.
[5] (a) Andersson, P. G.; Backvall, J. E. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.:Negishi, E., Wiley-Interscience, New York, 2002, p. 1859.
(b) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518.
(c) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004, Vol. 2, p. 699.
(d) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.:Negishi, E., Wiley-Interscience, New York, 2002, p. 1051.
[6] (a) Ranerand, K. D.; Ward, A. D. Aust. J. Chem. 1991, 44, 1749.
(b) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
(c) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469.
[7] (a) Schultz, D. M.; Wolfe, J. P. Org. Lett. 2010, 12, 1028.
(b) Caddick, S.; Koe, W. Tetrahedron Lett. 2002, 43, 9347.
(c) Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491.
(d) Lu, T.; Lu, Z.; Ma, Z. X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862.
[8] Cho, C. S.; Kim, J. S.; Oh, B. H. Tetrahedron 2000, 56, 7747.
[9] Cui, X. M. Chlor-Alkali Ind. 2000, 5, 172192(in Chinese). (崔小明, 氯碱工业, 2000, 5, 17219.)
[10] (a) Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795.
(b) Lu, Z.; Ma, S. M. Angew. Chem., Int. Ed. 2008, 47, 258.
(c) Luo, J.; Jiang, H. F. Chin. J. Org. Chem. 2008, 28, 187(in Chinese). (罗洁, 江焕峰, 有机化学, 2008, 28, 187.)
(d) Li, Y.; Zheng, Y.; Tian, F.; Zhang, Y. J.; Zhang, W. Chin. J. Org. Chem. 2009, 29, 1487(in Chinese). (李亚玺, 郑玉林, 田丰涛, 张勇健, 张万斌, 有机化学, 2009, 29, 1487.)
(e) Lee, O. Y.; Law, K. L.; Yang, D. Org. Lett. 2009, 11, 3302.
(f) Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596.
(g) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
[11] Lee, O. Y.; Law, K. L.; Yang, D. Org. Lett. 2009, 11, 3302.
[12] (a) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
(b) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
(c) Zhou, C. Y.; Zhu, S. F.; Wang, L. X., Zhou, Q. L. J. Am. Chem. Soc. 2010, 132, 10955.
(d) Holmes, M.; Schwartz, L. A.; Krische, M. J. Chem. Rev. 2018, 118, 6026.
[13] (a) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C. G.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
(b) Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314.
[14] (a) Bäckvall, J. E.; Nordberg, R. E.; Nyström, J. E.; Hoegberg, T.; Ulff, B. J. Org. Chem. 1981, 46, 3479.
(b) You, S. L.; Zhu, X. Z.; Luo, Y. M.; Hou, X. L.; Dai, L. X. J. Am. Chem. Soc. 2001, 123, 7471.
(c) Nagano, T.; Kobayashi, S. J. Am. Chem. Soc. 2009, 131, 4200.
(d) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
(e) Dubovyk, I.; Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2013, 78, 1559.
(f) Cai, A. J.; Guo, W. S.; Martínez-Rodríguez, L.; Kleij, A. W. J. Am. Chem. Soc. 2016, 138, 14194.
(g) Li, Y. G.; Li, L.; Yang, M. Y.; Kantchev, E. A. B. J. Org. Chem. 2017, 82, 4907.
[15] (a) Trost, B. M.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427.
(b) Evans, P.; Grange, R.; Clizbe, E. Synthesis 2016, 48, 2911.
(c) Guo, W.; Cai, A.; Xie, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2017, 56, 11797.
(d) Xia, C.; Shen, J.; Liu, D.; Zhang, W. Org. Lett. 2017, 19, 4251.
(e) Wang, Y. N.; Wang, B. C.; Zhang, M. M.; Gao, X. W.; Li, T. R.; Lu, L. Q.; Xiao, W. J. Org. Lett. 2017, 19, 4094.
[16] Yao, L.; Wang, C. J. Adv. Synth. Catal. 2015, 357, 384.
[17] Lu, B.; Feng, B.; Ye, H.; Chen, J. R.; Xiao, W. J. Org. Lett. 2018, 20, 3473.
[18] Ouyang, K.; Xi, Z. Acta Chim. Sinica 2013, 71, 13(in Chinese). (欧阳昆冰, 席振峰, 化学学报, 2013, 71, 13.)

Options
文章导航

/

〈 〉