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2021 , Vol. 41 >Issue 11: 4484 - 4492

DOI: https://doi.org/10.6023/cjoc202104039

研究论文

铱催化的苯甲酰胺和磷酰叠氮在离子液体中的C—H键胺化反应

  • 宁资慧 ,
  • 彭欣华 ,
  • 白瑞 ,
  • 刘珊珊 ,
  • 李卓 ,
  • 焦林郁
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  • a 西北大学化工学院 西安 710069
    b 陕西科技大学化学与化工学院 陕西省轻化工助剂重点实验室 西安 710021

收稿日期: 2021-04-18

  修回日期: 2021-06-30

  网络出版日期: 2021-07-20

基金资助

国家自然科学基金(21901150); 陕西省自然科学基金(2019JQ-787)

收起

Iridium Catalyzed C—H Amidation of Benzamides with Phosphoryl Azides in Ionic Liquids

  • Zihui Ning ,
  • Xinhua Peng ,
  • Rui Bai ,
  • Shanshan Liu ,
  • Zhuo Li ,
  • Linyu Jiao
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  • a School of Chemical Engineering, Northwest University, Xi'an 710069
    b College of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science & Technology, Xi'an 710021
* Corresponding authors. E-mail: ;

Received date: 2021-04-18

  Revised date: 2021-06-30

  Online published: 2021-07-20

Supported by

National Natural Science Foundation of China(21901150); Natural Science Foundation of Shaanxi Province(2019JQ-787)

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摘要

磷酰胺是天然产物和生物活性分子中常见结构, 也是合成化学中重要的中间体. 报道了一种直接、简单、高效且相对绿色的过渡金属铱催化的C—H键胺基化反应, 以弱配位的苯甲酰胺类化合物和磷酰叠氮化合物分别为反应底物和胺基化试剂, 在离子液体中实现了目标转化, 得到中等到优良的分离产率, 表现出良好的官能团耐受性和较高的区域选择性, 并提出了反应的可能机理. 该催化体系的建立丰富了磷酰胺的合成途径, 拓展了离子液体类绿色介质在C—H键官能化中的应用.

关键词： 过渡金属; 离子液体; 碳氢活化; 胺基化; 区域选择性; 磷酰叠氮

本文引用格式

宁资慧 , 彭欣华 , 白瑞 , 刘珊珊 , 李卓 , 焦林郁 . 铱催化的苯甲酰胺和磷酰叠氮在离子液体中的C—H键胺化反应[J]. 有机化学, 2021 , 41(11) : 4484 -4492 . DOI: 10.6023/cjoc202104039

Abstract

Phosphoramides are common structures in natural products and bioactive molecules. Additionally, they are also important intermediates in synthetic chemistry. In this paper, a direct, simple, efficient and relatively greener transition metal iridium catalyzed C—H bond amidation was reported. The target conversion was achieved in ionic liquids using weakly coordinated benzamides and phosphoryl azides as substrates and amidation reagents, respectively. Moderate to excellent isolated yields were obtained, showing good functional group tolerance and high regioselectivity. Furthermore, a possible mechanism of the reaction was proposed. The establishment of the catalytic system enriches the synthesis protocols of phosphoramides and extends the application of ionic liquids as green media in the C—H bond functionalization.

Key words： transition metal; ionic liquids; hydrocarbon activation; amidation; regioselectivity; phosphoryl azid

参考文献

[1]
(a) Schwarz, D. M. C.; Williams, S. K.; Dillenburg, M.; Wagner, C. R.; Gestwicki, J. E. ACS Med. Chem. Lett. 2020, 11, 1704.
[1]
(b) Serpi, M.; Bibbo, R.; Rat, S.; Roberts, H.; Hughes, C.; Caterson, B.; Alcaraz, M. J.; Gibert, A. T.; Verson, C. R. A.; McGuigan, C. J. Med. Chem. 2012, 55, 4629.
[1]
(c) Roush, R. F.; Nolan, E. M.; Löhr, F.; Walsh, C. T. J. Am. Chem. Soc. 2008, 130, 3603.
[2]
(a) Ullmann, F.; Dtsch, B. Chem. Ges. 1903, 36, 2382.
[2]
(b) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954.
[3]
(a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
[3]
(b) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
[3]
(c) Dorel, R.; Grugel, C. P.; Haydl, A. M. Angew. Chem., Int. Ed. 2019, 58, 17118.
[4]
(a) Chen, J.-Q.; Li, J.-L.; Dong, Z.-B. Adv. Synth. Catal. 2020, 362, 3311.
[4]
(b) West, M. J.; Fyfe, J. W. B.; Vantourout, J. C.; Watson, A. J. B. Chem. Rev. 2019, 119, 12491.
[5]
(a) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247.
[5]
(b) Wang, X.; Gao, J.; Xu, X.; Fang, P.; Mei, T. Chin. J. Org. Chem. 2021, 41, 384. (in Chinese)
[5]
(王向阳, 高君青, 徐学涛, 方萍, 梅天胜, 有机化学, 2021, 41, 384.)
[5]
(c) Ouyang, B.; Zheng, Y.; Xia, K.; Xu, X.; Wang, Y. Chin. J. Org. Chem. 2020, 40, 1188. (in Chinese)
[5]
(欧阳班来, 郑燕霞, 夏克坚, 徐小玲, 王艺, 有机化学, 2020, 40, 1188.)
[5]
(d) Wu, M.; Huang, X.; Zhang, H.; Li, P. Chin. J. Org. Chem. 2019, 39, 3114. (in Chinese)
[5]
(吴梅, 黄新平, 张海兵, 李鹏飞, 有机化学, 2019, 39, 3114.)
[5]
(e) Sun, Y.; Ding, Q.; Yu, Y.; He, Y.; Huang, F. Chin. J. Org. Chem. 2019, 39, 3363. (in Chinese)
[5]
(孙义明, 丁奇峰, 于杨, 何益得, 黄菲, 有机化学, 2019, 39, 3363.)
[5]
(f) Luo, F. Chin. J. Org. Chem. 2019, 39, 3084. (in Chinese)
[5]
(罗飞华, 有机化学, 2019, 39, 3084.)
[6]
(a) Nguyen, K. X.; Pham, P. H.; Nguyen, T. T.; Yang, C.-H.; Pham, H. T. B.; Nguyen, T. T.; Wang, H.; Phan, N. T. S. Org. Lett. 2020, 22, 9751.
[6]
(b) Zhou, C.; Zhao, J.; Guo, W.; Jiang, J.; Wang, J. Org. Lett. 2019, 21, 9315.
[7]
(a) Ng, K.-H.; Zhou, Z.; Yu, W.-Y. Chem. Commun. 2013, 49, 7031.
[7]
(b) Zhou, B.; Du, J.; Yang, Y.; Li, Y. Org. Lett. 2013, 15, 2934.
[7]
(c) Grohmann, C.; Wang, H.; Glorius, F. Org. Lett. 2012, 14, 656.
[8]
(a) Mei, R.; Loup, J.; Ackermann, L. ACS Catal. 2016, 6, 793.
[8]
(b) Liang, Y.; Liang, Y.-F.; Tang, C.; Yuan, Y.; Jiao, N. Chem. Eur. J. 2015, 21, 16395.
[8]
(c) Park, J.; Chang, S. Angew. Chem., Int. Ed. 2015, 54, 14103.
[8]
(d) Ding, J.; Jiang, W.; Bai, H.-Y.; Ding, T.-M.; Gao, D. F.; Bao, X. G.; Zhang, S.-Y. Chem. Commun. 2018, 54, 8889.
[8]
(e) Huang, J.; Ding, J.; Ding, T.-M.; Zhang, S. Y.; Wang, Y. Q.; Sha, F.; Zhang, S.-Y.; Wu, X.-Y.; Li, Q. Org. Lett. 2019, 21, 7342.
[9]
(a) Patel, P.; Chang, S. Org. Lett. 2014, 16, 3328.
[9]
(b) Patel, P; Chang, S. ACS Catal. 2015, 5, 853.
[10]
(a) Lee, J.; Jin, S.; Kim, D.; Hong, S. H.; Chang, S. J. Am. Chem. Soc. 2021, 143, 5191.
[10]
(b) Dong, X.; Ma, P.; Zhang, T.; Jalani, H. B.; Li, G.; Lu, H. J. Org. Chem. 2020, 85, 13096.
[10]
(c) Kim, H.; Park, J.; Kim, J. G.; Chang, S. Org. Lett. 2014, 16, 5466.
[10]
(d) Kim, J. Y.; Park, S. H.; Ryu, J.; Cho, S. H.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110.
[11]
(a) Xiao, W.; Zhou, C.-Y.; Che, C.-M. Chem. Commun. 2012, 48, 5871.
[11]
(b) Pan, C.; Jin, N.; Zhang, H.; Han, J.; Zhu, C. J. Org. Chem. 2014, 79, 9427.
[11]
(c) Pan, C. D.; Wang, Y.; Wu, C.; Yu, J.-T. Org. Biomol. Chem. 2018, 16, 3711.
[12]
(a) Muntzeck, M.; Pippert, F.; Wilhelm, R. Tetrahedron 2020, 76, 131314.
[12]
(b) Kong, X.; Xu, B. Asian J. Org. Chem. 2019, 8, 1862.
[12]
(c) Li, J.; Zhou, L.; Wang, Y.; Ma, Q.; Lei, Y.; Lai, R.; Luo, Y.; Hai, L.; Wu, Y. Eur. J. Org. Chem. 2019, 2019, 7448.
[13]
Ma, Q.; Yu, X.; Lai, R.; Lv, S.; Dai, W.; Zhang, C.; Wang, X.; Wang, Q.; Wu, Y. ChemSusChem 2018, 11, 3672.
[14]
Jiao, L.-Y.; Ning, Z.-H.; Hong, Q.; Peng, X.-H.; Yin, X.-M.; Liu, S.; Chen, H.; Li, Z.; Sun, M.; Ma, X.-X. RSC Adv. 2020, 10, 29712.
[15]
(a) Jiao, L.-Y.; Zhang, Z.; Yin, X.-M.; Li, Z.; Ma, X.-X. J. Catal. 2019, 379, 39.
[15]
(b) Jiao, L.-Y.; Zhang, Z.; Hong, Q.; Ning, Z.-H.; Liu, S.; Sun, M.; Hao, Q.; Xu, L.; Li, Z.; Ma, X.-X. Mol. Catal. 2020, 494, 111120.
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