酰基镍作为关键中间体参与的酰基还原制备酮的研究进展
收稿日期: 2023-04-19
修回日期: 2023-06-01
网络出版日期: 2023-06-14
基金资助
国家自然科学基金(22071111); 伊犁师范大学科研(2023YSYB009)
Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones
Received date: 2023-04-19
Revised date: 2023-06-01
Online published: 2023-06-14
Supported by
National Natural Science Foundation of China(22071111); Yili Normal University Scientific Research Project(2023YSYB009)
齐云鹏 , 林登凯 , 陈良安 . 酰基镍作为关键中间体参与的酰基还原制备酮的研究进展[J]. 有机化学, 2023 , 43(11) : 3861 -3875 . DOI: 10.6023/cjoc202304025
Acyl-Ni has emerged as an important synthetic intermediate in organic synthesis. In recent years, a strategy for the synthesis of ketones with acyl-Ni species as a key intermediate for synthesizing ketones has attracted broad attention. Compared with the traditional cross-coupling involving organometallic reagents, reductive acylation using the in situ generated acyl-Ni species with various carbon electrophiles exhibits many notable advantages, such as mild conditions, high step economy, widely functional group tolerance, and environmentally friendly. This review focuses on the recent advances in Ni-catalyzed reductive acylation of various carbon electrophiles with a broad range of carboxylic acids or carboxylic acid derivatives.
Key words: acyl nickel; reductive acylation; nickel catalysis; ketones; electrophiles
| [1] | Battaglia, U.; Moody, C. J. Nat. Prod. 2010, 73, 1938. |
| [2] | Chong, Y. M.; Yin, W. F.; Ho, C. Y.; Mustafa, M. R.; Hadi, A. H. A.; Awang, K.; Narrima, P.; Koh, C.-L.; Appleton, D. R.; Chan, K.-G. J. Nat. Prod. 2011, 74, 2261. |
| [3] | Zhu, D. L.; Young, D. J.; Li, H. X. Synthesis 2020, 52, 3493. |
| [4] | Wotal, A. C.; Weix, D. J. Org. Lett. 2012, 14, 1476. |
| [5] | Wu, F.; Lu, W. B.; Qian, Q.; Ren, Q. H.; Gong, H. G. Org. Lett. 2012, 14, 3044. |
| [6] | Lu, W.; Liang, Z.; Zhang, Y.; Wu, F.; Qian, Q.; Gong, H. G. Synthesis 2013, 45, 2234. |
| [7] | Zhao, X.; Tu, H.-Y.; Guo, L.; Zhu, S.; Qing, F.-L.; Chu, L. Nat. Commun. 2018, 9, 3488. |
| [8] | Scattolin, T.; Deckers, K.; Schoenebeck, F. Org. Lett. 2017, 19, 5740. |
| [9] | Munoz, S. B.; Dang, H.; Ispizua-Rodriguez, X.; Mathew, T.; Prakash, G. K. S. Org. Lett. 2019, 21, 1659. |
| [10] | Pan, F.-F.; Guo, P.; Li, C.-L.; Su, P.; Shu, X.-Z. Org. Lett. 2019, 21, 3701. |
| [11] | Wang, J.; Hoerrner, M. E.; Watson, M. P.; Weix, D. J. Angew. Chem., Int. Ed. 2020, 59, 13484. |
| [12] | Pulikottil, F. T.; Pilli, R.; Suku, R. V.; Rasappan, R. Org. Lett. 2020, 22, 2902. |
| [13] | Liao, J.; Basch, G. H.; Hoerrner, M. E.; Talley, M. R.; Boscoe, B. P.; Tucker, J. W.; Garnsey, M. R.; Waston, M. P. Org. Lett. 2019, 21, 2941. |
| [14] | Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442. |
| [15] | Lin, D.; Chen, Y.; Dong, Z.; Pei, P.; Ji, H.; Tai, L.; Chen, L.-A. CCS Chem. 2023, 5, 1386. |
| [16] | Wu, B.-B.; Xu, J.; Bian, K.-J.; Gao, Q.; Wang, X.-S. J. Am. Chem. Soc. 2022, 144, 6543. |
| [17] | Wu, J.; Wu, H.; Liu, X.; Zhang, Y.; Huang, G.; Zhang, C. Org. Lett. 2022, 24, 4322. |
| [18] | Hoyos, P.; Sinisterra, J.-V.; Molinari, F.; Alcántara, A. R.; Domínguez De María, P. Acc. Chem. Res. 2010, 43, 288. |
| [19] | Jennings, L. K.; Robertson, L. P.; Rudolph, K. E.; Munn, A. L.; Carroll, A. R. J. Nat. Prod. 2019, 82, 2620. |
| [20] | Ji, H.; Lin, D.; Tai, L.; Li, X.; Shi, Y.; Han, Q.; Chen, L.-A. J. Am. Chem. Soc. 2022, 144, 23019. |
| [21] | Goo?en, L. J.; Rodríguez, N.; Goo?en, K. Angew. Chem., Int. Ed. 2008, 47, 3100. |
| [22] | Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645. |
| [23] | Ni, S.; Padial, N. M.; Kingston, C.; Vantourout, J. C.; Schmitt, D. C.; Edwards, J. C.; Kruszy, M. M.; Merchant, R. R.; Mykhailiuk, P. K.; Sanchez, B. B.; Yang, S.; Perry, M. A.; Gallego, G. M.; Mousseau, J. J.; Collins, M. R.; Cherney, R. J.; Lebed, P. S.; Chen, J. S.; Qin, T.; Baran, P. S. J. Am. Chem. Soc. 2019, 141, 6726. |
| [24] | Jiao, K.-J.; Ma, C.; Liu, D.; Qiu, H.; Cheng, B.; Mei, T.-S. Org. Chem. Front. 2021, 8, 6603. |
| [25] | Ruzi, R.; Liu, K.; Zhu, C.; Xie, J. Nat. Commun. 2020, 11, 3312. |
| [26] | Li, Y.; Shao, Q.; He, H.; Zhu, C.; Xue, X.-S.; Xie, J. Nat. Commun. 2022, 13, 10. |
| [27] | Zhang, L.; Chen, S.; He, H.; Li, W.; Zhu, C.; Xie, J. Chem. Commun. 2021, 57, 9064. |
| [28] | He, J.; Song, P.; Xu, X.; Zhu, S.; Wang, Y. ACS Catal. 2019, 9, 3253. |
| [29] | Jiang, X.; Sheng, F.-T.; Zhang, Y.; Deng, G.; Zhu, S. J. Am. Chem. Soc. 2022, 144, 21448. |
| [30] | Davidsen, S. K.; May, P. D.; Summers, J. B. J. Org. Chem. 1991, 56, 5482. |
| [31] | Hie, L.; Nathel, N. F. F.; Shah, T. K.; Baker, E. L.; Hong, X.; Yang, Y. F.; Liu, P.; Houk, K. N.; Garg, N. K. Nature 2015, 524, 79. |
| [32] | Simmons, B. J.; Weires, N. A.; Dander, J. E.; Garg, N. K. ACS Catal. 2016, 6, 3176. |
| [33] | Weires, N. A.; Baker, E. L.; Garg, N. K. Nat. Chem. 2016, 8, 75. |
| [34] | Hu, J.; Zhao, Y.; Liu, J.; Zhang, Y.; Shi, Z. Angew. Chem., Int. Ed. 2016, 55, 8718. |
| [35] | Ni, S.; Zhang, W.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2017, 19, 2536. |
| [36] | Yu, C.-G.; Matsuo, Y. Org. Lett. 2020, 22, 950. |
| [37] | Zhuo, J.; Zhang, Y.; Li, Z.; Li, C. ACS Catal. 2020, 10, 3895. |
| [38] | Kerackian, T.; Reina, A.; Bouyssi, D.; Monteiro, N.; Amgoune, A. Org. Lett. 2020, 22, 2240. |
| [39] | Kerackian, T.; Bouyssi, D.; Pilet, G.; Médebielle, M.; Monteiro, N.; Vantourout, J. C.; Amgoune, A. ACS Catal. 2022, 12, 12315. |
| [40] | Ai, Y.; Ye, N.; Wang, Q.; Yahata, K.; Kishi, Y. Angew. Chem., Int. Ed. 2017, 56, 10791. |
| [41] | Wu, X.; Han, J.; Xia, S.; Li, W.; Zhu, C.; Xie, J. CCS Chem. 2022, 4, 2469. |
| [42] | Yang, F.; Ding, D.; Wang, C. Org. Lett. 2020, 22, 9203. |
| [43] | Xi, X.; Luo, Y.; Li, W.; Xu, M.; Zhao, H.; Chen, Y.; Zheng, S.; Qi, X.; Yuan, W. Angew. Chem., Int. Ed. 2022, 61, e202114731. |
| [44] | Sun, Y.; Su, L.; Tong, W.; Yao, K.; Gong, H. Synlett 2021, 32, 1762. |
| [45] | Xu, S.; Wang, K.; Kong, W. Org. Lett. 2019, 21, 7498. |
| [46] | Shi, R.; Hu, X. Angew. Chem., Int. Ed. 2019, 58, 7454. |
| [47] | Chen, H.; Yue, H.; Zhu, C.; Rueping, M. Angew. Chem., Int. Ed. 2022, e202204144. |
| [48] | Chen, J.; Zhu, S. J. Am. Chem. Soc. 2021, 143, 14089. |
| [49] | Chen, J.; Deng, G.; Wang, Y.; Zhu, S. Chin. J. Chem. 2023, 41, 294. |
| [50] | Zheng, M.; Xue, W.; Xue, T.; Gong, H. Org. Lett. 2016, 18, 6152. |
| [51] | Zhu, Z.; Gong, Y.; Tong, W.; Xue, W.; Gong, H. Org. Lett. 2021, 23, 2158. |
/
| 〈 |
|
〉 |