Chinese Journal of Organic Chemistry >
Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide
Received date: 2021-04-10
Revised date: 2021-06-07
Online published: 2021-06-17
Supported by
Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology(BM2012110); Natural Science Foundation for Colleges and Universities in Jiangsu Province(20KJA530003); Jiangsu Key Laboratory of Biomass Energy and Material(JSBEM202018)
An efficient heterogeneous catalytic system based on NiGa layered double oxide (Ni3Ga-LDO) for the C—N coupling between isochroman and primary arylamines has been described. Various primary arylamines were tolerated by the catalytic system, and good to excellent yields for the corresponding coupled products could be obtained. The results indicated that Ni species played the key role in the oxidative cross-coupling process, and the catalyst had good catalytical and structural stability. The protocol provides an effective alternative approach to construct C—N bond.
Junfeng Qian , Xiaoting Tian , Zhong Wu , Jie Yao , Hui Wang , Weiyou Zhou . Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3668 -3674 . DOI: 10.6023/cjoc202104021
| [1] | (a) Xu, Z.; Zheng, Y.; Wang, Z.; Shao, X.; Wang, Y. Chem. Commun. 2019, 55, 15089. |
| [1] | (b) Nasresfahani, Z.; Kassaee, M. Z. Appl. Organomet. Chem. 2021, 35(1), e6032. |
| [1] | (c) Luo, N. H.; Zhong, Y. H.; Wen, H. L.; Luo, R. ACS Omega 2020, 5, 27723. |
| [2] | (a) Ghorai, M. K.; Nanaji, Y. J. Org. Chem. 2013, 78, 3867. |
| [2] | (b) Larsen, A. F.; Ulven, T. Chem. Commun. 2014, 50, 4997. |
| [2] | (c) Xie, J. W.; Wang, X. C.; Wu, F. T.; Zhang, J. Chin. J. Org. Chem. 2019, 39, 3026. (in Chinese). |
| [2] | ( 谢建伟, 汪小创, 吴丰田, 张洁, 有机化学, 2019, 39, 3026.) |
| [2] | (d) Yao, D. D.; Zhang, J. L.; Xu, L. Chin. J. Org. Chem. 2020, 40, 1673. (in Chinese). |
| [2] | ( 姚丹丹, 张金利, 徐亮, 有机化学, 2020, 40, 1673.) |
| [3] | (a) Irrgang, T.; Kempe, R. Chem. Rev. 2020, 120, 9583. |
| [3] | (b) Montes-Andre?s, H.; Leo, P.; Mun?oz, A.; Rodríguez-Diéguez, A.; Orcajo, G.; Choquesillo-Lazarte, D.; Martos, C.; Martínez, F.; Botas, J. A.; Calleja, G. Inorg. Chem. 2020, 59, 15733. |
| [3] | (c) Bhoge, B. A.; Mala, P.; Kurian, J. S.; Srinivasan, V.; Saraogi, I. Chem. Commun. 2020, 56, 13832. |
| [3] | (d) Ravi, K.; Advani, J. H.; Bankar, B. D.; Singh, A. S.; Biradar, A. V. New J. Chem. 2020, 44, 18714. |
| [3] | (e) Petersen, A. R.; Lauridsen, J. M. V.; Lee, J. W. Eur. J. Org. Chem. 2020, 47, 7368. |
| [3] | (f) Yan, F.; Cai, S.; Wen, W.; Wen, W.; Li, B. J.; Wang, L. S.; Zhu, L. Chin. J. Org. Chem. 2020, 40, 1874. (in Chinese). |
| [3] | ( 严沣, 蔡爽, 闻武, 文蔚, 李博解, 汪连生, 朱磊, 有机化学, 2020, 40, 1874.) |
| [4] | (a) Aneeja, T.; Neetha, M.; Afsinaa, C. M. A.; Anilkumar, G. RSC Adv. 2020, 10, 34429. |
| [4] | (b) Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301. |
| [4] | (c) Wang, G.; Wang, J. T.; Zhao, B.; Chen, H.; Zhang, P. K.; Han, S. L. Tetrahedron Lett. 2020, 61, 151426. |
| [4] | (d) Zhang, X. L.; Pan, G. F.; Zhu, X. Q.; Guo, R. L.; Gao, Y. R.; Wang, Y. Q. Org. Lett. 2019, 21, 2731. |
| [4] | (e) Basle?, O.; Li, C. J. Chem. Commun. 2009, 27, 4124. |
| [4] | (f) Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317. |
| [4] | (g) Wusiman, A.; Hudabaierdi, R. Tetrahedron Lett. 2019, 60, 681. |
| [4] | (h) Liu, Y. X.; Wang, C.; Xue, D.; Xiao, M.; Li, C. Q.; Xiao, J. L. Chem.-Eur. J. 2017, 23, 3051. |
| [4] | (i) Brzozowski, M.; Forni, J. A.; Savage, G. P.; Polyzos, A. Chem. Commun. 2015, 51, 334. |
| [4] | (j) Sun, Y. M.; Ding, Q. F.; Yu, Y.; He, Y. D.; Huang, F. Chin. J. Org. Chem. 2019, 39, 3363. (in Chinese). |
| [4] | ( 孙义明, 丁奇峰, 于杨, 何益得, 黄菲, 有机化学, 2019, 39, 3363.) |
| [4] | (k) Rana, P.; Gaur, R.; Gupta, R.; Arora, G.; Jayashree, A.; Sharama, R. K. Chem. Commun. 2019, 55, 7402. |
| [4] | (l) Xie, J.; Li, H. M.; Zhou, J. C.; Cheng, Y. X.; Zhu, C. J. Angew. Chem. Int. Ed. 2012, 51, 1252. |
| [4] | (m) Ratnikov, M. O.; Doyle, M. P.; J. Am. Chem. Soc. 2013, 135, 1549. |
| [4] | (n) Patil, M. R.; Dedhia, N. P.; Kapdi, A. R.; Kumar, A. V. J. Org. Chem. 2018, 83, 4477. |
| [4] | (o) Kumar, R. A.; Saidulu, G.; Prasad, K. R.; Kumar, G. S.; Sridhar, B.; Reddy, K. R. Adv. Synth. Catal. 2012, 354, 2985. |
| [4] | (p) Cao, M.; Mao, Y.; Huang, J. C.; Ma, Y. D.; Liu, L. Tetrahedron Lett. 2019, 60, 1075. |
| [5] | (a) Martin, P.; Consroe, P. Science 1976, 194, 965. |
| [5] | (b) Groot, M. J. D.; Alex, A. A.; Jones, B. C. J. Med. Chem. 2002, 45, 1983. |
| [5] | (c) Yamaori, S.; Kushihara, M.; Yamamoto, I.; Watanabe, Y. Biochem. Pharmacol. 2010, 79, 1691. |
| [6] | (a) Lehmann, F.; Pettersen, A.; Currier, E. A.; Sherbukhin, V.; Olsson, R.; Hacksell, U., Luthman, K. J. Med. Chem. 2006, 49, 2232. |
| [6] | (b) Maier, C. A.; Wünsch, B. J. Med. Chem. 2002, 45, 438. |
| [7] | Feng, J.; Lv, M. F.; Lu, G. P.; Cai, C. Org. Chem. Front. 2015, 2, 60. |
| [8] | Chen, D.; Pan, F.; Gao, J.; Yang, J. Synlett 2013, 24, 2085. |
| [9] | (a) Zhou, W. Y.; Lu, W. M. Z.; Wang, H.; Xia, Z. Z.; Zhai, S. Y.; Zhang, Z.; Ma, Y. J.; He, M. Y.; Chen, Q. Appl. Catal. A, Gen. 2020, 604, 117771. |
| [9] | (b) Sun, Z. H.; Xia, Z. Z.; Wang, A. W.; Wang, H.; Zhang, Z.; Zhou, W. Y.; Qian, J. F.; He, M. Y. Tetrahedron Lett. 2020, 61, 152254. |
| [10] | Chen, Z. W.; Liu, B. T.; Liang, P.; Luo, H. Q.; Zheng, J.; Wen, X. W.; Liu, T. G.; Luo, G. T.; Ye, M. ACS Omega 2019, 4, 281. |
| [11] | Kumar, R. A.; Maheswari, C. U.; Ghantasala, S.; Jyothi, C.; Reddy, K. R. Adv. Synth. Catal. 2011, 353, 401. |
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