Chinese Journal of Organic Chemistry >
Ligand-Free Iron-Catalyzed Intramolecular Amination of C(sp3)—H Bond for the Synthesis of Imidazolinones
Received date: 2021-04-26
Revised date: 2021-05-09
Online published: 2021-05-14
Supported by
National Natural Science Foundation of China(21971198); National Natural Science Foundation of China(21772148)
Transition-metal-nitrenoids intramolecular C—H insertion is one of the most effective methods to synthesize nitrogen-containing heterocycles. Using 2-azido-N,N-dibenzylacetamides as substrates, an iron-catalyzed intramolecular C(sp3)—H bond amination reaction under ligand-free and external oxidant-free conditions has been developed. A series of imidazolinones were synthesized in moderate to good yields.
Linyang Wu , Dayou Zhong , Wenbo Liu . Ligand-Free Iron-Catalyzed Intramolecular Amination of C(sp3)—H Bond for the Synthesis of Imidazolinones[J]. Chinese Journal of Organic Chemistry, 2021 , 41(10) : 4083 -4087 . DOI: 10.6023/cjoc202104054
| [1] | Trowbridge, A.; Walton, S. M.; Gaunt, M. J. Chem. Rev. 2020, 120, 2613. |
| [2] | Hazelard, D.; Nocquet, P.; Compain, P. Org. Chem. Front. 2017, 4, 2500. |
| [3] | Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564. |
| [4] | Baumgartner, L. M.; Dennis, J. M.; White, N. A.; Buchwald, S. L.; Jensen, K. F. Org. Process Res. Dev. 2019, 23, 1594. |
| [5] | Dai, L. Prog. Chem. 2018, 30, 1257. (in Chinese) |
| [5] | (戴立信, 化学进展, 2018, 30, 1257.) |
| [6] | Cai, Q.; Zhou, W. Chin. J. Chem. 2020, 38, 879. |
| [7] | Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247. |
| [8] | Wang, P.; Deng, L. Chin. J. Chem. 2018, 36, 1222. |
| [9] | Plietker, B.; Röske, A. Catal. Sci. Technol. 2019, 9, 4188. |
| [10] | Liu, Y.; You, T.; Wang, H. X.; Tang, Z.; Zhou, C. Y.; Che, C.-M. Chem. Soc. Rev. 2020, 49, 5310. |
| [11] | Shi, D.; Bao, H.; Xu, Z.; Liu, Y. Chin. J. Org. Chem. 2017, 37, 1290. (in Chinese) |
| [11] | (施冬冬, 鲍汉扬, 徐峥, 刘运奎, 有机化学, 2017, 37, 1290.) |
| [12] | Xu, L.; Xu, H.; Lin, H.; Dai, H. Chin. J. Org. Chem. 2018, 38, 1940. (in Chinese) |
| [12] | (徐琳琳, 徐辉, 林海霞, 戴辉雄, 有机化学, 2018, 38, 1940.) |
| [13] | Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036. |
| [14] | Liang, L.; Lü, H.; Yu, Y.; Wang, P.; Zhang, J. Dalton Trans. 2012, 41, 1457. |
| [15] | Liu, Y.; Guan, X.; Wong, E. L.; Liu, P.; Huang, J.; Che, C.-M. J. Am. Chem. Soc. 2013, 135, 7194. |
| [16] | Wang, H.; Li, Y.; Wang, Z.; Lou, J.; Xiao, Y.; Qiu, G.; Hu, X.; Altenbach, H.; Liu, P. RSC Adv. 2014, 4, 25287. |
| [17] | Tseberlidis, G.; Zardi, P.; Caselli, A.; Cancogni, D.; Fusari, M.; Lay, L.; Gallo, E. Organometallics 2015, 34, 3774. |
| [18] | Thacker, N. C.; Lin, Z.; Zhang, T.; Gilhula, J. C.; Abney, C. W.; Lin, W.-B. J. Am. Chem. Soc. 2016, 138, 3501. |
| [19] | Alt, I. T.; Plietker, B. Angew. Chem., Int. Ed. 2016, 55, 1519. |
| [20] | Thacker, N. C.; Ji, P.; Lin, Z.; Urban, A.; Lin, W.-B. Faraday Discuss. 2017, 21, 303. |
| [21] | Shing, K.; Liu, Y.; Cao, B.; Chang, X.; You, T.; Che, C.-M. Angew. Chem., Int. Ed. 2018, 57, 11947. |
| [22] | Liu, Y.; You, T.; Wang, T.; Che, C.-M. Tetrahedron 2019, 75, 130607. |
| [23] | Du, Y.; Xu, Z.; Zhou, C.; Che, C.-M. Org. Lett. 2019, 21, 895. |
| [24] | Breslow, R.; Gellman, S. H. J. Chem. Soc., Chem. Commun. 1982, 1400. |
| [25] | King, E. R.; Betley, T. A. Inorg. Chem. 2009, 48, 2361. |
| [26] | Wang, Z.; Zhang, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2008, 10, 1863. |
| [27] | Shen, M.; Driver, T. G. Org. Lett. 2008, 10, 3367. |
| [28] | Bonnamour, J.; Bolm, C. Org. Lett. 2011, 13, 2012. |
| [29] | Nguyen, Q.; Nguyen, T.; Driver, T. G. J. Am. Chem. Soc. 2013, 135, 620. |
| [30] | Liu, Y.; Che, C.-M. Chem.-Eur. J. 2010, 16, 10494. |
| [31] | Zhao, X.; Liang, S.; Fan, X.; Yang, T.; Yu, W. Org. Lett. 2019, 21, 1559. |
| [32] | Liang, S.; Zhao, X.; Yang, T.; Yu, W. Org. Lett. 2020, 22, 1961. |
| [33] | Kweon, J.; Chang, S. Angew. Chem., Int. Ed. 2021, 60, 2909. |
| [34] | Prasanthi, A. V. G.; Begum, S.; Srivastava, H. K.; Tiwari, S. K.; Singh, R. ACS Catal. 2018, 8, 8369. |
| [35] | Zhou, Z.; Tan, Y.; Yamahira, T.; Ivlev, S.; Xie, X.; Riedel, R.; Hemming, M.; Kimura, M.; Meggers, E. Chem 2020, 6, 2024. |
| [36] | Zhong, D.; Wu, D.; Zhang, Y.; Lu, Z.; Usman, M.; Liu, W.; Lu, X.; Liu, W.-B. Org. Lett. 2019, 21, 5808. |
| [37] | Liu, W.; Zhong, D.; Yu, C.; Zhang, Y.; Wu, D.; Feng, Y.; Cong, H.; Lu, X.; Liu, W.-B. Org. Lett. 2019, 21, 2673. |
| [38] | Zhang, Y.; Zhong, D.; Usman, M.; Xue, P.; Liu, W.-B. Chin. J. Chem. 2020, 38, 1651. |
| [39] | Zhong, D.; Wu, L.-Y.; Wang, X.-Z.; Liu, W.-B. Chin. J. Chem. 2021, 39, 855. |
| [40] | Liang, S.; Zhao, X; Yang, T.; Yu, W. Org. Lett. 2020, 22, 1961. |
| [41] | Zhou, Z.; Chen, S.; Qin, J.; Nie, X.; Zheng, X.; Harms, K.; Riedel, R.; Houk, K. N.; Meggers, E. Angew. Chem., Int. Ed. 2019, 58, 1088. |
/
| 〈 |
|
〉 |
