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

doi:10.6023/cjoc202304025

摘要/Abstract

酰基镍是金属有机合成中的一类重要中间体, 近些年来, 以酰基镍为中间体的还原酰基化反应合成酮的策略引起了广泛地关注. 相较于金属亲核试剂参与的传统交叉偶联反应, 还原酰基化反应具有条件温和、步骤经济性高、官能团兼容性良好、环境友好等优点. 对近些年来镍催化羧酸或羧酸衍生物和各种亲电试剂的还原酰基化合成酮的最新研究进行了概述.

关键词: 酰基镍, 还原酰化, 镍催化, 酮, 亲电试剂

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

引用此文

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.

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.

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图/表 27

图式1. 酰基镍中间体参与的还原酰基化反应合成酮

Scheme 1. Synthesis of ketones by reductive acylation reactions via acyl nickel intermediates

图式2. 酰氯和烷基碘代物的还原酰基化反应

Scheme 2. Reductive acylation of acyl chlorides and alkyl iodides

图式3. 非活化烯烃、全氟烷基碘和酰氯的三组分还原酰基化反应

Scheme 3. Three-component reductive acylation of unactivate olefins, perfluoroalkyl iodides and acyl chlorides

图式4. 酰氟与烯基三氟甲磺酸酯的还原酰基化反应

Scheme 4. Reductive acylation of acyl fluorides and alkenyl trifluoromethanesulfonates

图式5. 酰卤与吡啶季铵盐的还原酰基化反应

Scheme 5. Reductive acylation of acyl halides and N-alkyl pyridinium salts

图式6. 烷基氯代物与酰氯的不对称还原酰基化反应

Scheme 6. Asymmetric reductive acylation of alkyl chlorides and acyl chlorides

图式7. 酰氯与α-三氟烷基溴的不对称还原酰基化反应

Scheme7 Asymm. etric reductive acylation of acyl chlorides and α-trifluoroalkyl bromides Asymmetric reductive acylation of acyl chlorides and α-trifluoroalkyl bromides

图式8. 酰氯与α-酰氧基溴代物的不对称还原酰基化反应

Scheme 8. Asymmetric reductive acylation of acyl chlorides and α-bromobenzoates

图式9. 羧酸与三级卤代烷烃或糖基卤的还原酰基化反应

Scheme 9. Reductive acylation of carboxylic acids with tertiary alkyl or glycosyl halides

图式10. 羧酸与酰胺的脱羧还原酰基化反应

Scheme 10. Decarboxylative reductive acylation of amides and carboxylic acids

图式11. 羧酸与烷基卤代物的迁移还原酰基化反应

Scheme 11. Migratory reductive acylation of alkyl halides and carboxylic acids

图式12. 光镍协同催化羧酸脱羧还原酰基化反应

Scheme 12. Light-promoted Ni-catalyzed decarboxylative reductive acylation of carboxylic acids

图式13. 羧酸与卤代烷烃或烯烃的迁移还原酰基化反应

Scheme 13. Migratory reductive acylation of carboxylic acids with olefins or alkyl halides

图式14. 酰胺的还原酰基化反应

Scheme 14. Reductive acylation of amides

图式15. 酰基咪唑与芳基溴代物或烷基溴代物的还原酰基化反应

Scheme 15. Reductive acylation of acylimidazoles with alkyl bromides or aryl bromides

图式16. 酰胺与烷基溴代物的还原酰基化反应

Scheme 16. Reductive acylation of amides and alkyl bromides

图式17. 镍/锆催化烷基碘代物与吡啶硫酯的还原酰基化反应

Scheme 17. Nickel/Zirconium catalyzed reductive acylation of alkyl iodides and pyridine thioesters

图式18. 光镍协同催化羧酸和硫酯的脱羧还原酰基化反应

Scheme 18. Light-promoted Ni-catalyzed decarboxylative reductive acylation of carboxylic acids and thioesters

图式19. 酚酯与烷基溴化物的还原酰基化反应

Scheme 19. Reductive acylation of phenolic esters and alkyl bromides

图式20. 光镍协同催化吡啶酯与邻苯二甲酰亚胺酯的还原酰基化反应

Scheme 20. Light-promoted Ni-catalyzed reductive acylation of pyridyl esters and NHPI esters

图式21. 草酸二苯酯与烷基溴代物或烷基对甲苯磺酸酯的还原酰基化反应

Scheme 21. Reduction acylation reaction of diphenyl oxalate with alkyl bromide or alkyl p-toluenesulfonate

图式22. 烷基卤代物、烯烃与氯甲酸酯的三组分还原酰基化反应

Scheme 22. Three-component reductive acylation of alkyl halides, olefins and chloroformates

图式23. 烷基卤代物与氯甲酸酯的三组分还原酰基化反应

Scheme 23. Three-component reductive acylation of alkyl halides and chloroformates

图式24. 芳基卤化物、烷基卤代物和氯甲酸酯的三组分还原酰基化反应

Scheme 24. Three-component reductive acylation of aryl halides, alkyl halides and chlorofomates

图式25. 烯烃的三组分还原氢酰基化反应

Scheme 25. Three-component reductive hydrocarbonylation of alkenes

图式26. 烷基卤代物与氯甲酸酯的还原酰基化反应

Scheme 26. Reductive acylation of alkyl halides and chloroformates

图式27. 芳基三氟甲磺酸酯与硫代碳酸酯的还原酰基化反应

Scheme 27. Reductive acylation of aryl triflates and thiocarbo- nates

参考文献 51

[1]	Battaglia, U.; Moody, C. J. Nat. Prod. 2010, 73, 1938. doi: 10.1021/np100298m pmid: 20836523
[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. doi: 10.1021/np100872k pmid: 21910441
[3]	Zhu, D. L.; Young, D. J.; Li, H. X. Synthesis 2020, 52, 3493. doi: 10.1055/s-0040-1707183
[4]	Wotal, A. C.; Weix, D. J. Org. Lett. 2012, 14, 1476. doi: 10.1021/ol300217x
[5]	Wu, F.; Lu, W. B.; Qian, Q.; Ren, Q. H.; Gong, H. G. Org. Lett. 2012, 14, 3044. doi: 10.1021/ol3011198
[6]	Lu, W.; Liang, Z.; Zhang, Y.; Wu, F.; Qian, Q.; Gong, H. G. Synthesis 2013, 45, 2234. doi: 10.1055/s-00000084
[7]	Zhao, X.; Tu, H.-Y.; Guo, L.; Zhu, S.; Qing, F.-L.; Chu, L. Nat. Commun. 2018, 9, 3488. doi: 10.1038/s41467-018-05951-6
[8]	Scattolin, T.; Deckers, K.; Schoenebeck, F. Org. Lett. 2017, 19, 5740. doi: 10.1021/acs.orglett.7b02516 pmid: 29023131
[9]	Munoz, S. B.; Dang, H.; Ispizua-Rodriguez, X.; Mathew, T.; Prakash, G. K. S. Org. Lett. 2019, 21, 1659. doi: 10.1021/acs.orglett.9b00197
[10]	Pan, F.-F.; Guo, P.; Li, C.-L.; Su, P.; Shu, X.-Z. Org. Lett. 2019, 21, 3701. doi: 10.1021/acs.orglett.9b01164
[11]	Wang, J.; Hoerrner, M. E.; Watson, M. P.; Weix, D. J. Angew. Chem., Int. Ed. 2020, 59, 13484. doi: 10.1002/anie.v59.32
[12]	Pulikottil, F. T.; Pilli, R.; Suku, R. V.; Rasappan, R. Org. Lett. 2020, 22, 2902. doi: 10.1021/acs.orglett.0c00554 pmid: 32216317
[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. doi: 10.1021/acs.orglett.9b01014
[14]	Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442. doi: 10.1021/ja402922w pmid: 23634932
[15]	Lin, D.; Chen, Y.; Dong, Z.; Pei, P.; Ji, H.; Tai, L.; Chen, L.-A. CCS Chem. 2023, 5, 1386. doi: 10.31635/ccschem.022.202202076
[16]	Wu, B.-B.; Xu, J.; Bian, K.-J.; Gao, Q.; Wang, X.-S. J. Am. Chem. Soc. 2022, 144, 6543. doi: 10.1021/jacs.2c01422
[17]	Wu, J.; Wu, H.; Liu, X.; Zhang, Y.; Huang, G.; Zhang, C. Org. Lett. 2022, 24, 4322. doi: 10.1021/acs.orglett.2c01208
[18]	Hoyos, P.; Sinisterra, J.-V.; Molinari, F.; Alcántara, A. R.; Domínguez De María, P. Acc. Chem. Res. 2010, 43, 288. doi: 10.1021/ar900196n
[19]	Jennings, L. K.; Robertson, L. P.; Rudolph, K. E.; Munn, A. L.; Carroll, A. R. J. Nat. Prod. 2019, 82, 2620. doi: 10.1021/acs.jnatprod.9b00551
[20]	Ji, H.; Lin, D.; Tai, L.; Li, X.; Shi, Y.; Han, Q.; Chen, L.-A. J. Am. Chem. Soc. 2022, 144, 23019. doi: 10.1021/jacs.2c10072
[21]	Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100. doi: 10.1002/anie.v47:17
[22]	Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645. doi: 10.1021/ja510653n
[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. doi: 10.1021/jacs.9b02238
[24]	Jiao, K.-J.; Ma, C.; Liu, D.; Qiu, H.; Cheng, B.; Mei, T.-S. Org. Chem. Front. 2021, 8, 6603. doi: 10.1039/D1QO01219C
[25]	Ruzi, R.; Liu, K.; Zhu, C.; Xie, J. Nat. Commun. 2020, 11, 3312. doi: 10.1038/s41467-020-17224-2
[26]	Li, Y.; Shao, Q.; He, H.; Zhu, C.; Xue, X.-S.; Xie, J. Nat. Commun. 2022, 13, 10. doi: 10.1038/s41467-021-27507-x
[27]	Zhang, L.; Chen, S.; He, H.; Li, W.; Zhu, C.; Xie, J. Chem. Commun. 2021, 57, 9064. doi: 10.1039/D1CC04188F
[28]	He, J.; Song, P.; Xu, X.; Zhu, S.; Wang, Y. ACS Catal. 2019, 9, 3253. doi: 10.1021/acscatal.9b00521
[29]	Jiang, X.; Sheng, F.-T.; Zhang, Y.; Deng, G.; Zhu, S. J. Am. Chem. Soc. 2022, 144, 21448. doi: 10.1021/jacs.2c10785
[30]	Davidsen, S. K.; May, P. D.; Summers, J. B. J. Org. Chem. 1991, 56, 5482. doi: 10.1021/jo00018a059
[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. doi: 10.1038/nature14615
[32]	Simmons, B. J.; Weires, N. A.; Dander, J. E.; Garg, N. K. ACS Catal. 2016, 6, 3176. doi: 10.1021/acscatal.6b00793 pmid: 32257581
[33]	Weires, N. A.; Baker, E. L.; Garg, N. K. Nat. Chem. 2016, 8, 75. doi: 10.1038/nchem.2388
[34]	Hu, J.; Zhao, Y.; Liu, J.; Zhang, Y.; Shi, Z. Angew. Chem., Int. Ed. 2016, 55, 8718. doi: 10.1002/anie.v55.30
[35]	Ni, S.; Zhang, W.; Mei, H.; Han, J.; Pan, Y. Org. Lett. 2017, 19, 2536. doi: 10.1021/acs.orglett.7b00831
[36]	Yu, C.-G.; Matsuo, Y. Org. Lett. 2020, 22, 950. doi: 10.1021/acs.orglett.9b04497
[37]	Zhuo, J.; Zhang, Y.; Li, Z.; Li, C. ACS Catal. 2020, 10, 3895. doi: 10.1021/acscatal.0c00246
[38]	Kerackian, T.; Reina, A.; Bouyssi, D.; Monteiro, N.; Amgoune, A. Org. Lett. 2020, 22, 2240. doi: 10.1021/acs.orglett.0c00442 pmid: 32148046
[39]	Kerackian, T.; Bouyssi, D.; Pilet, G.; Médebielle, M.; Monteiro, N.; Vantourout, J. C.; Amgoune, A. ACS Catal. 2022, 12, 12315. doi: 10.1021/acscatal.2c03268
[40]	Ai, Y.; Ye, N.; Wang, Q.; Yahata, K.; Kishi, Y. Angew. Chem., Int. Ed. 2017, 56, 10791. doi: 10.1002/anie.v56.36
[41]	Wu, X.; Han, J.; Xia, S.; Li, W.; Zhu, C.; Xie, J. CCS Chem. 2022, 4, 2469. doi: 10.31635/ccschem.021.202101197
[42]	Yang, F.; Ding, D.; Wang, C. Org. Lett. 2020, 22, 9203. doi: 10.1021/acs.orglett.0c03342
[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. doi: 10.1002/anie.v61.3
[44]	Sun, Y.; Su, L.; Tong, W.; Yao, K.; Gong, H. Synlett 2021, 32, 1762. doi: 10.1055/a-1550-7935
[45]	Xu, S.; Wang, K.; Kong, W. Org. Lett. 2019, 21, 7498. doi: 10.1021/acs.orglett.9b02788
[46]	Shi, R.; Hu, X. Angew. Chem., Int. Ed. 2019, 58, 7454. doi: 10.1002/anie.v58.22
[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. doi: 10.1021/jacs.1c07851
[49]	Chen, J.; Deng, G.; Wang, Y.; Zhu, S. Chin. J. Chem. 2023, 41, 294. doi: 10.1002/cjoc.v41.3
[50]	Zheng, M.; Xue, W.; Xue, T.; Gong, H. Org. Lett. 2016, 18, 6152. pmid: 27934381
[51]	Zhu, Z.; Gong, Y.; Tong, W.; Xue, W.; Gong, H. Org. Lett. 2021, 23, 2158. doi: 10.1021/acs.orglett.1c00313