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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 3: 1216 - 1223

DOI: https://doi.org/10.6023/cjoc202009014

ARTICLES

Gram-Scale Synthesis of Polymeric Carbon Nitride-Supported Copper: A Practical Catalyst for Ullmann-Type C—N Coupling Modifying Secondary Pyrimidin-2-amines without Additional Ligand

  • Yangyang Sun ,
  • Gang Feng ,
  • Chao Chen ,
  • Yonghong Liu ,
  • Xu Zhang
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  • a School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002
    b Jiangsu College of Tourism, Yangzhou, Jiangsu 225000
* Corresponding authors. E-mail: ;

Received date: 2020-09-06

  Revised date: 2020-09-29

  Online published: 2020-10-22

Supported by

Priority Academic Program Development of Jiangsu Higher Education Institutions

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Abstract

Cu/polymeric carbon nitride (PCN) can be prepared in 10 g scale by calcining Cu(NO3)2 with the melamine precursor at 550 ℃. X-ray photoelectron spectroscopy (XPS) analysis demonstrated that copper in the material was in Cu(I) form and it could catalyze the Ullmann-type C—N coupling reactions of pyrimidin-2-amine derivatives with aryl halides without additional ligand. As a heterogeneous catalyst, the material was recoverable and could be reused for at least five times without deactivation. This material was found to be even more active than traditional Cu(I) catalysts and Pd catalysts, affording an opportunity to develop the efficient and practical novel catalyst reagent for the synthesis of medicines containing pyrimidin-2-amine moieties in pharmaceutical industry.

Key words： polymeric carbon nitride (PCN); copper; catalysis; Ullmann-type C—N coupling reaction; pyrimidin-2-amine

Cite this article

Yangyang Sun , Gang Feng , Chao Chen , Yonghong Liu , Xu Zhang . Gram-Scale Synthesis of Polymeric Carbon Nitride-Supported Copper: A Practical Catalyst for Ullmann-Type C—N Coupling Modifying Secondary Pyrimidin-2-amines without Additional Ligand[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1216 -1223 . DOI: 10.6023/cjoc202009014

References

[1]
(a) Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564.
[1]
(b) Hartwig, J. F. Nature 2008, 455, 314.
[1]
(c) Monnier, F.; Taillefer, M. Angew. Chem.. Int. Ed. 2009, 48, 6954.
[1]
(d) Dorel, R.; Grugel, C. P.; Haydl, A. M. Angew. Chem.. Int. Ed. 2019, 58, 17118.
[1]
(e) Chen, Y.; Jing, X.; Yu, L. Chin. J. Org. Chem. 2020, 40, 2570. (in Chinese)
[1]
(陈颖, 景崤壁, 俞磊, 有机化学, 2020, 40, 2570.)
[2]
(a) Chen, T.; Yan, M.; Zheng, C.; Yuan, J.; Xu, S.; Chen, R.; Huang, W. Chin. J. Chem. 2015, 33, 961.
[2]
(b) Bhunia, S.; Vijay Kumar, S.; Ma, D. J. Org. Chem. 2017, 82, 12603.
[2]
(b) Ohyoshi, T.; Akemoto, K.; Taniguchi, A.; Ishihara, T.; Kigoshi, H. New J. Chem. 2019, 43, 18442.
[2]
(c) Garcia, R. C.; Pech, M. J.; Sommer, R.; Gorman, C. B. J. Org. Chem. 2019, 84, 15079.
[2]
(d) Thomas, G. T.; Janusson, E.; Zijlstra, H. S.; McIndoe, J. S. Chem. Commun. 2019, 55, 11727.
[2]
(e) Hemmati, S.; Kamangar, S. A.; Yousefi, M.; Salehi, M. H.; Hekmati, M. Appl. Organomet. Chem. 2020, 34, e5611.
[2]
(f) Ge, X.; Ge, M.; Chen, X.; Qian, C.; Liu, X.; Zhou, S. Mol. Catal. 2020, 484, 110726.
[3]
Zhang, X.; Sun, J.; Chen, T.; Yang, C.; Yu, L. Synlett 2016, 27, 2233.
[4]
Erickson, G.; Guo, J.; McClure, M.; Mitchell, M.; Salaun, M.; Whitehead, A. Tetrahedron Lett. 2014, 55, 6007.
[5]
Maskrey, T. S.; Kristufek, T.; LaPorte, M. G.; Nyalapatla, P. R.; Wipf, P. Synlett 2019, 30, 471.
[6]
(a) Yang, T.; Yin, L.; He, M.; Wei, W.; Cao, G.; Ding, X.; Wang, Y.; Zhao, Z.; Yu, T.; Zhao, H.; Zhang, D. Chem. Commun. 2019, 55, 14343.
[6]
(b) Sun, J.; Hu, J.; Han, J.; Yuan, G.; Guo, R. Langmuir 2019, 35, 12704.
[6]
(c) Zou, L.; Hou, C.; Liu, Z.; Pang, H.; Xu, Q. J. Am. Chem. Soc. 2018, 140, 15393.
[6]
(d) Cheng, Z.; Sun, W. Chin. Chem. Lett. 2016, 27, 81.
[6]
(e) Dao, T. D.; Han, G.; Arai, N.; Nabatame, T.; Wada, Y.; Hoang, C. V.; Aono, M.; Nagao, T. Phys. Chem. Chem. Phys. 2015, 17, 7395.
[7]
(a) Zhang, D.; Wei, Z.; Yu, L. Sci. Bull. 2017, 62, 1325.
[7]
(b) Chen, C.; Cao, K.; Wei, Z.; Zhang, Q.; Yu, L. Mater. Lett. 2018, 226, 63.
[8]
(a) Yu, L.; Han, Z.; Ding, Y. Org. Process Res. Dev. 2016, 20, 2124.
[8]
(b) Yu, L.; Huang, Y.; Wei, Z.; Ding, Y.; Su, C.; Xu, Q. J. Org. Chem. 2015, 80, 8677.
[9]
(a) Cao, H.; Yang, Y.; Chen, X.; Liu, J.; Chen, C.; Yuan, S.; Yu, L. Chin. Chem. Lett. 2020, 31, 1887.
[9]
(b) Yang, Y.; Li, M.; Cao, H.; Zhang, X.; Yu, L. Mol. Catal. 2019, 474, 110450.
[9]
(c) Wang, F.; Xu, L.; Sun, C.; Yu, L.; Xu, Q. Appl. Organomet. Chem. 2018, 32, e4505.
[9]
(d) Wang, Y.; Wu, Z.; Li, Q.; Zhu, B.; Yu, L. Catal. Sci. Technol. 2017, 7, 3747.
[9]
(e) Wang, F.; Xu, L.; Huang, J.; Wu, S.; Yu, L.; Xu, Q.; Fan, Y. Mol. Catal. 2017, 432, 99.
[10]
(a) Yang, Y.; Xu, B.; He, J.; Shi, J.; Yu, L.; Fan, Y. Appl. Catal.. A 2020, 590, 117353.
[10]
(b) Yang, Y.; Xu, B.; He, J.; Shi, J.; Yu, L.; Fan, Y. Appl. Organomet. Chem. 2019, 33, e5204.
[10]
(c) Zhou, H.; Gong, J.; Xu, B.; Yu, L.; Fan, Y. Appl. Catal.. A 2016, 527, 30.
[11]
(a) Tong, Q.; Zhao, S.; Liu, Y.; Xu, B.; Yu, L.; Fan, Y. Appl. Organomet. Chem. 2020, 34, e538.
[11]
(b) Zhao, S.; Xu, B.; Yu, L.; Fan, Y. Chin. Chem. Lett. 2018, 29, 884.
[11]
(c) Zhao, S.; Xu, B.; Yu, L.; Fan, Y. Chin. Chem. Lett. 2018, 29, 475.
[12]
(a) Liu, C.; Mao, J.; Zhang, X.; Yu, L. Catal. Commun. 2020, 133, 105828.
[12]
(b) Chen, X.; Mao, J.; Liu, C.; Chen, C.; Cao, H.; Yu, L. Chin. Chem. Lett. 2020, 31, 3205.
[12]
(c) Deng, S.; Meng, T.; Xu, B.; Gao, F.; Ding, Y.; Yu, L.; Fan, Y. ACS Catal. 2016, 6, 5807.
[12]
(d) Deng, S.; Zhuang, K.; Xu, B.; Ding, Y.; Yu, L.; Fan, Y. Catal. Sci. Technol. 2016, 6, 1772.
[12]
(e) Tong, Q.; Zong, A.; Gong, W.; Yu, L.; Fan, Y. RSC Adv. 2016, 6, 86663.
[13]
(a) Xia, Y.-T.; Wu, J.-J.; Zhang, C.-Y.; Mao, M.; Ji, Y.-G.; Wu, L. Org. Lett. 2019, 21, 6383.
[13]
(b) Xia, Y.-T.; Xie, X.-Y.; Cui, S.-H.; Ji, Y.-G.; Wu, L. Chem. Commun. 2019, 55, 11699.
[13]
(c) Xia, Y.-T.; Ma, J.; Wang, X.-D.; Yang, L.; Wu, L. Catal. Sci. Technol. 2017, 7, 5515.
[13]
(d) Zhang, Y.; Zhu, J.; Xia, Y.-T.; Sun, X.-T.; Wu, L. Adv. Synth. Catal. 2016, 358, 3039.
[14]
(a) Wang, Y.; Wang, X.; Antonietti, M. Angew. Chem.. Int. Ed. 2012, 51, 68.
[14]
(b) Yang, H.; Xu, B.; Yuan, S.; Zhang, Q.; Zhang, M.; Ohno, T. Appl. Catal., B 2019, 243, 513.
[14]
(c) Cao, K.; Deng, X.; Chen, T.; Zhang, Q.; Yu, L. J. Mater. Chem. A 2019, 7, 10918.
[14]
(d) Fan, X.; Yao, Y.; Xu, Y.; Yu, L.; Qiu, C. ChemCatChem 2019, 11, 2596.
[15]
(a) Liu, Y.; Wang, J.-P. Org. Biomol. Chem. 2011, 9, 6873.
[15]
(b) Wan, J.-P.; Jing, Y. Beilstein J. Org. Chem. 2015, 11, 2209.
[15]
(c) Li, X.; Lin, J.; Wang, J.; Li, Z.; Gu, Q.; Liu, X. Acta Chim. Sinica 2018, 76, 878. (in Chinese)
[15]
(李雪飞, 林进顺, 王建, 李忠良, 顾强帅, 刘心元, 化学学报, 2018, 76, 878.)
[15]
(d) Duan, X.; Liu, N.; Wang, J.; Ma, J. Chin. J. Org. Chem. 2019, 39, 661. (in Chinese)
[15]
(段希焱, 刘宁, 王佳, 马军营, 有机化学, 2019, 39, 661.)
[15]
(e) Xie, J.; Wang, X.; Wu, F.; Zhang, J. Chin. J. Org. Chem. 2019, 39, 3026. (in Chinese)
[15]
(谢建伟, 汪小创, 吴丰田, 张洁, 有机化学, 2019, 39, 3026.)
[15]
(f) Cai, Q.; Zhou, W. Chin. J. Chem. 2020, 38, 879.
[15]
(g) Luo, T.; Wan, J.-P.; Liu, Y. Org. Chem. Front. 2020, 7, 1107.
[15]
(h) vali, Shaik, B.; Seelam,, M.; Tamminana,, R.; Kammela,, P. R. Tetrahedron 2019, 75, 3865.
[15]
(i) Yao, D.; Zhang, J.; Xu, L. Chin. J. Org. Chem. 2020, 40, 1673. (in Chinese)
[15]
(姚丹丹, 张金利, 徐亮, 有机化学, 2020, 40, 1673.)
[15]
(j) Chen, C.; Cao, Z.; Zhang, X.; Li, Y.; Yu, L.; Jiang, X. Chin. J. Chem. 2020, 38, 1045.
[15]
(k) Fan, X.; Yi, R.; Wang, F.; Zhang, X.; Xu, Q.; Yu, L. Chin. J. Org. Chem. 2018, 38, 2736. (in Chinese)
[15]
(范昕, 易容, 王芳, 张旭, 徐清, 俞磊, 有机化学, 2018, 38, 2736.)
[16]
(a) Zhang, J.; Cao, K.; Zhang, X.; Zhang, Q. Appl. Organomet. Chem. 2020, 34, e5377.
[16]
(b) Cao, H.; Sun, Y.; Wang, F.; Zhang, X. Microporous Mesoporous Mater. 2020, 295, 109972.
[17]
(a) Scott, S. L. ACS Catal. 2018, 8, 8597.
[17]
(b) Duong, U. T.; Gade, A. B.; Plummer, S.; Gallou, F.; Handa, S. ACS Catal. 2019, 9, 10963.
[18]
Wang, M.; Cheng, X.; Ni, Y. Dalton Trans. 2019, 48, 823.
[19]
(a) Chen, C.; Cao, Y.; Wu, X.; Cai, Y.; Liu, J.; Xu, L.; Ding, K.; Yu, L. Chin. Chem. Lett. 2020, 31, 1078.
[19]
(b) Chen, Y.; Deng, X.; Jing, X.; Zhou, H. Chin. J. Org. Chem. 2020, 40, 4147. (in Chinese)
[19]
(陈颖, 邓鑫, 景崤壁, 周宏伟, 有机化学, 2020, 40, 4147.)
[19]
(c) Zheng, Y.; Wu, A.; Ke, Y.; Cao, H.; Yu, L. Chin. Chem. Lett. 2019, 30, 937.
[19]
(d) Zhang, H.; Han, M.; Yang, C.; Yu, L.; Xu, Q. Chin. Chem. Lett. 2019, 30, 263.
[20]
(a) Johansson Seechurn, C. C. C.; Parisel,, S. L.; Colacot,, T. J. J. Org. Chem. 2011, 76, 7918.
[20]
(b) Elbert, B. L.; Farley, A. J. M.; Gorman, T. W.; Johnson, T. C.; Genicot, C.; Lallemand, B.; Pasau, P.; Flasz, J.; Castro, J. L.; MacCoss, M.; Paton, R. S.; Schofield, C. J.; Smith, M. D.; Willis, M. C.; Dixon, D. J. Chem.-Eur. J. 2017, 23, 14733.
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