SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 11: 3861 - 3875

DOI: https://doi.org/10.6023/cjoc202304025

Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones

  • Yunpeng Qi ,
  • Dengkai Lin ,
  • Liang-An Chen
Expand
  • a University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Key Laboratory of Pollutant Chemistry and Enviromental Treatment, School of Chemistry and Environmental Science, Yili Normal University, Yining, Xinjiang 835000
    b School of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210023
†These authors contributed equally to this work.
* E-mail:

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)

Fold

Abstract

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

Cite this article

Yunpeng Qi , Dengkai Lin , Liang-An Chen . Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones[J]. Chinese Journal of Organic Chemistry, 2023 , 43(11) : 3861 -3875 . DOI: 10.6023/cjoc202304025

References

[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.
Options
Outlines

/

〈 〉