Chinese Journal of Organic Chemistry >
Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides
Received date: 2024-01-01
Revised date: 2024-02-07
Online published: 2024-03-05
Supported by
National Natural Science Foundation of China(21901192); National Natural Science Foundation of China(22271225); Natural Science Foundation of Hubei Province(2019CFB12); Natural Science Foundation of Hubei Province(2022CFB221)
A nickel-catalyzed reductive trans-arylative cyclization of 1,6-enynes with aryl halides has been developed. This transformation avoids the use of stoichiometric organometallic reagents and features mild conditions, good functional group tolerance and broad substrate scope. This method serves as an efficient platform for the synthesis of various carbo- and heterocycles, which are abundant in many natural products and biologically active compounds.
Key words: nickel catalysis; reductive cross-coupling; 1,6-enyne; tandem cyclization
Yunxin Xing , Denghong Yan , Shun Wen , Jie Bu , Kun Shen . Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1938 -1948 . DOI: 10.6023/cjoc202401001
| [1] | For selected reviews on transition metal-catalyzed tandem cyclization reactions, see: (a) Miura, T.; Murakami, M. Chem. Commun. 2007, 217. |
| [1] | (b) Youn, S. W. Eur. J. Org. Chem. 2009, 2597. |
| [1] | (c) Tian, P; Dong, H.; Lin, Q. ACS Catal. 2012, 2, 95. |
| [1] | (d) Han, X.; Lu, X. Synlett 2018, 29, 2461. |
| [1] | (e) Gillbard, S. M.; Lam, H. W. Chem.-Eur. J. 2022, 28, e202104230. |
| [2] | (a) Ikeda, S.; Cui, D.; Sato, Y. J. Org. Chem. 1994, 59, 6877. |
| [2] | (b) Cui, D.; Tsuzuki, T.; Miyake, K.; Ikeda, S.; Sato, Y. Tetrahedron 1998, 54, 1063. |
| [2] | (c) Ikeda, S.; Miyashita, H.; Sato, Y. Organometallics 1998, 17, 4316. |
| [3] | (a) Zhu, G.; Zhang, Z. Org. Lett. 2003, 5, 3645. |
| [3] | (b) Zhu, G.; Tong, X.; Cheng, J.; Sun, Y.; Li, D.; Zhang, Z. J. Org. Chem. 2005, 70, 1712. |
| [4] | (a) Miura, T.; Shimada, M.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1094. |
| [4] | (b) Miura, T.; Shimada, M.; Murakami, M. Chem.-Asian J. 2006, 1, 868. |
| [5] | Shen, K.; Han, X.; Lu, X.; Hu, Z. Tetrahedron Lett. 2017, 58, 3768. |
| [6] | Yap, C; Lenagh-Snow, G. M. J.; Karad, S. N.; Lewis, W.; Diorazio, L. J.; Lam, H. W. Angew. Chem., Int. Ed. 2017, 56, 8216. |
| [7] | Wang, K.; Chen, J.; Liu, W.; Kong, W. Angew. Chem., Int. Ed. 2022, 61, e202201574. |
| [8] | (a) Knappke, C. E. I.; Grupe, S.; G?rtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828. |
| [8] | (b) Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793. |
| [8] | (c) Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242. |
| [8] | (d) Wang, X.; Dai, Y.; Gong, H. Top. Curr. Chem. 2016, 374, 43. |
| [8] | (e) Richmond, E.; Moran, J. Synthesis 2018, 50, 499. |
| [8] | (f) Poremba, K.; Dibrell, S.; Reisman, S. ACS Catal. 2020, 10, 8237. |
| [8] | (g) Yi, L.; Ji, T.; Chen, K.; Chen, X.; Rueping, M. CCS Chem. 2022, 4, 9. |
| [8] | (h) Li, T.; Cheng, X.; Lu, J.; Wang, H.; Fang, Q.; Lu, Z. Chin. J. Chem. 2022, 40, 1033. |
| [8] | (i) Zhang, L.; Du, Q.; Luo, Y.; Wang, Y.; Gao, F.; Ye, Y.; Zhang, W. Chin. J. Chem. 2023, 41, 3003. |
| [9] | (a) Derosa, J.; Apolinar, O.; Kang, T.; Tran, V. T.; Engle, K. M. Chem. Sci. 2020, 11, 4287. |
| [9] | (b) Tu, H.-Y.; Zhu, S.; Qing, F.-L.; Chu, L. Synthesis 2020, 52, 1346. |
| [9] | (c) Zhu, C.; Yue, H.; Chu, L.; Rueping, M. Chem. Sci. 2020, 11, 4051. |
| [9] | (d) Bottcher, S.; Hutchinson, L.; Wilger, D. Synthesis 2020, 52, 2807. |
| [9] | (e) Qi, X.; Diao, T. ACS Catal. 2020, 10, 8542. |
| [9] | (f) Liu, W.; Kong, W. Org. Chem. Front. 2020, 7, 394. |
| [9] | (g) Zhu, S.; Zhao, X.; Li, H.; Chu, L. Chem. Soc. Rev. 2021, 50, 10836. |
| [9] | (h) Pan, Q.; Ping, Y.; Kong, W. Acc. Chem. Res. 2023, 56, 515. |
| [10] | (a) Rayabarapu, D. K.; Cheng, C.-H. Chem. Commun. 2002, 942. |
| [10] | (b) Rayabarapu, D. K.; Yang, C.-H.; Cheng, C.-H. J. Org. Chem. 2003, 68, 6726. |
| [10] | (c) Durandetti, M.; Hardou, L.; Clement, M.; Maddaluno, J. Chem. Commun. 2009, 4753. |
| [10] | (d) Durandetti, M.; Hardou, L.; Lhermet, R.; Rouen, M.; Maddaluno, J. Chem.-Eur. J. 2011, 17, 12773. |
| [10] | (e) Wang, X.; Liu, Y.; Martin, R. J. Am. Chem. Soc. 2015, 137, 6476. |
| [10] | (f) García-Domínguez, A.; Li, Z.; Nevado, C. J. Am. Chem. Soc. 2017, 139, 6835. |
| [10] | (g) Shu, W.; García-Domínguez, A.; Quirós, M. T.; Mondal, R.; Cárdenas, D. J.; Nevado, C. J. Am. Chem. Soc. 2019, 141, 13812. |
| [10] | (h) Han, S.; Liu, S.; Liu, L.; Ackermann, L.; Li, J. Org. Lett. 2019, 21, 5387. |
| [10] | (i) Ping, Y.; Wang, K.; Pan, Q.; Ding, Z.; Zhou, Z.; Guo, Y.; Kong, W. ACS Catal. 2019, 9, 7335. |
| [10] | (j) Zhou, Z.; Chen, J.; Chen, H.; Kong, W. Chem. Sci. 2020, 11, 10204. |
| [10] | (k) Zhan, Y.; Xiao, N.; Shu, W. Nat. Commun. 2021, 12, 928. |
| [10] | (l) Zhou, Y.; Meng, H.; Shu, W. Chem. Sci. 2022, 13, 4930. |
| [11] | Shimkin, K.; Montgomery, J. J. Am. Chem. Soc. 2018, 140, 7074. |
| [12] | Zhou, Z.; Liu, W.; Kong, W. Org. Lett. 2020, 22, 6982. |
| [13] | Shen, K.; Han, X.; Lu, X. Org. Lett. 2012, 14, 1756. |
| [14] | For selected examples on Ni-catalyzed anti-carbometallative cyclizations, see: (a) Clarke, C.; Incerti-Pradillos, C. A.; Lam, H. W. J. Am. Chem. Soc. 2016, 138, 8068. |
| [14] | (b) Zhang, X.; Xie, X.; Liu, Y. Chem. Sci. 2016, 7, 5815. |
| [14] | (c) Karad, S. N.; Panchal, H.; Clarke, C.; Lewis, W.; Lam, H. W. Angew. Chem., Int. Ed. 2018, 57, 9122. |
| [14] | (d) Gillbard, S. M.; Chung, C.; Karad, S. N.; Panchal, H.; Lewis, W.; Lam, H. W. Chem. Comm. 2018, 54, 11769. |
| [14] | (e) Kumar, G. R.; Kumar, R.; Rajesh, M.; Reddy, M. S. Chem. Commun. 2018, 54, 759. |
| [14] | (f) Iqbal, N.; Iqbal, N.; Maiti, D.; Cho, E. J. Angew. Chem., Int. Ed. 2019, 58, 15808. |
| [14] | (g) Di Sanza, R.; Nguyen, T. L. N.; Iqbal, N.; Argent, S. P.; Lewis, W.; Lam, H. W. Chem. Sci. 2020, 11, 2401. |
| [14] | (h) Gillbard, S. M.; Green, H.; Argent, S. P.; Lam, H. W. Chem. Commun. 2021, 57, 4436. |
| [14] | (i) Green, H.; Argent, S. P.; Lam, H. W. Chem.-Eur. J. 2021, 27, 5897. |
| [14] | (g) Min, K. H.; Iqbal, N.; Cho, E. J. Org. Lett. 2022, 24, 989. |
| [14] | (k) Lu, Z.; Hu, X.; Zhang, H.; Zhang, X.; Cai, J.; Usman, M.; Cong, H.; Liu, W.-B. J. Am. Chem. Soc. 2020, 142, 7328. |
| [14] | (l) Tambe, S. D.; Ka, C. H.; Hwang, H. S.; Bae, J.; Iqbal, N.; Cho, E. J. Angew. Chem., Int. Ed. 2022, 61, e202203494. |
/
| 〈 |
|
〉 |