镍催化不对称酰基化反应研究进展

doi:10.6023/cjoc202211032

摘要/Abstract

α-手性羰基化合物是天然产物和药物中的重要结构单元, 也是反应性最为丰富的重要合成中间体. 过渡金属催化不对称酰基化反应是构建该重要结构单元的高效方法之一, 近些年来, 具有独特催化活性的丰产金属镍催化剂也被广泛应用于不对称羰基化合物的合成. 综述了近些年来镍催化不对称酰基化反应领域的新研究进展, 主要包括镍催化不对称烷基-酰基偶联反应、烯烃不对称氢酰基化反应以及烯烃不对称酰基官能团化反应等.

关键词: 镍催化, 不对称酰基化, 氢酰基化, 烯烃

Chiral αα-carbonyl compounds are important structural units in natural products and pharmaceuticals and versatile synthetic building blocks in organic synthesis. Transition metal-catalyzed asymmetric acylation reaction is one of the most straightforward methods for preparing these compounds. In particular, significant progress has been made in the area of nickel-catalyzed asymmetric acylation reaction, due to the unique properties of nickel catalysts. The latest progress of nickel-catalyzed asymmetric acylation reaction, including nickel-catalyzed asymmetric alkyl-acyl cross-coupling reaction, asymmetric hydroacylation of alkene and asymmetric acyl-functionalization alkene, is summarized.

Key words: nickel catalysis, asymmetric acylation, hydroacylation, alkene

引用此文

张妍妍, 张珠珠, 朱圣卿, 储玲玲. 镍催化不对称酰基化反应研究进展[J]. 有机化学, 2023, 43(3): 1023-1035.

Yanyan Zhang, Zhuzhu Zhang, Shengqing Zhu, Lingling Chu. Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1023-1035.

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图/表 21

图式1. 镍催化不对称酰基化反应

Scheme 1. Nickel-catalyzed asymmetric acylation reactions

图式2. α-取代内酰胺的不对称酰基化反应

Scheme 2. Asymmetric acylation of α-substituted lactams

图式3. 烷基氯与酰氯的不对称还原偶联

Scheme 3. Asymmetric reductive coupling of acid chlorides and secondary alkyl chlorides

图式4. α-三氟甲基烷基溴的不对称还原酰基反应

Scheme 4. Asymmetric reductive acylation of α-trifluoromethyl brormides

图式5. α-三氟甲基烷基溴的不对称酰基化反应

Scheme 5. Asymmetric acylation of αα-trifluoromethyl brormides

图式6. 可见光/镍协同催化DHPs与对称酸酐的不对称交叉偶联反应

Scheme 6. Nickel/photoredox-catalyzed asymmetric acyl cross- coupling with DHPs and symmetrical anhydrides

图式7. 光/镍协同催化烷基胺C—H键不对称酰基化反应

Scheme 7. Asymmetric C—H acylation of alkylamines cataly- zed by nickel/photoredox

图式8. 光/镍协同催化苄基C(sp3)—H不对称酰基化反应

Scheme 8. Nickel/photoredox-catalyzed asymmetric benzylic C(sp3)—H acyltion

图式9. 烯烃不对称氢氨甲酰基化反应

Scheme 9. Asymmetric hydrocarbamoylations of alkenes

图式10. 烯烃三组分不对称还原氢酰基化反应

Scheme 10. Three-component asymmetric reductive hydroacylation of alkenes

图式11. 烯烃或卤代烃的不对称迁移还原酰基化

Scheme 11. Asymmetric migratory reductive acylation of olefins or alkyl halides

图式12. 非活化烯烃的不对称碳氨甲酰基化反应

Scheme 12. Asymmetric carbamoylation of unactivated alkenes

图式13. 烯烃的不对称还原碳氨甲酰基化反应

Scheme 13. Asymmetric reductive carbamoylation of alkenes

图式14. 烯烃的还原不对称碳酰化反应

Scheme 14. Asymmetric reductive carbo-acylation of alkenes

图式15. 烯烃的不对称还原双氨甲酰基化反应

Scheme 15. Asymmetric reductive dicarbamoylation of alkenes

图式16. 非活化烯烃的还原不对称氨甲酰基烷基化反应

Scheme 16. Asymmetric reductive carbamoyl-alkylation of un- activated alkenes

图式17. 非活化1,6-二烯的去对称化氨甲酰基-烷基化反应

Scheme 17. Desymmetric carbamoyl-alkylation of unactivated 1,6-dienes

图式18. 氨甲酰氯取代的内烯烃与烷基碘化物的不对称烷基-氨甲酰基化反应

Scheme 18. Asymmetric alkyl-carbamoylation of internal alkenes with alkyl iodides

图式19. 邻位烯丙基取代的芳氨基甲酰氯和烷基碘的不对称环化偶联反应

Scheme 19. Asymmetric cyclization of ortho-allyl substituted arylcarbamyl chlorides with alkyl iodines

图式20. 光/镍协同催化烯烃不对称酰基-氨甲酰基化反应

Scheme 20. Nickel/photoredox-catalyzed asymmetric acylcar- bamoylation of alkenes

图式21. 邻位氨基甲酰氯取代芳基烯烃的不对称碘代氨甲酰基化反应

Scheme 21. Asymmetric carbamoyl iodination of 1,1-disubsti- tuted styrenes

参考文献 30

[1]	(a) Harrington, P. J.; Lodewijk, E. Org. Process Res. Dev. 1997, 1, 72. doi: 10.1021/op960009e pmid: 19821577
	(b) Foley, K. F.; Cozzi, N. V. Drug Dev. Res. 2003, 60, 252. doi: 10.1002/(ISSN)1098-2299 pmid: 19821577
	(c) Carroll, F. I.; Blough, B. E.; Abraham, P.; Mills, A. C.; Holleman, J. A.; Wolckenhauer, S. A.; Decker, A. M.; Landavazo, A.; McElroy, K. T.; Navarro, H. A.; Gatch, M. B.; Forster, M. J. J. Med. Chem. 2009, 52, 6768. doi: 10.1021/jm901189z pmid: 19821577
[2]	(a) Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082. doi: 10.1021/cr9000836 pmid: 24555548
	(b) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676. doi: 10.1002/anie.200903424 pmid: 24555548
	(c) Pitts, C. R.; Lectka, T. Chem. Rev. 2014, 114, 7930. doi: 10.1021/cr4005549 pmid: 24555548
	(d) Wang, P.; Yang, D.; Liu, H. Chin. J. Org. Chem. 2021, 41, 3448. (in Chinese) doi: 10.6023/cjoc202104060 pmid: 24555548
	(王鹏, 杨妲, 刘欢, 有机化学, 2021, 41, 3448.) doi: 10.6023/cjoc202104060 pmid: 24555548
[3]	(a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234. doi: 10.1021/ar0201106 pmid: 28649462
	(b) MacMillan, D. W. C.; Watson, A. J. B. Inα-Functionalization of Carbonyl Compounds, StereoselectiveSynthesis 3,1st ed.ed., Vol. 3, Georg Thieme Verlag KG, Stuttgart, 2011, p. 675. pmid: 28649462
	(c) Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 9748. doi: 10.1002/anie.201109036 pmid: 28649462
	(d) Oliver, S.; Evans, P. A. Synthesis 2013, 45, 3179. doi: 10.1055/s-00000084 pmid: 28649462
	(e) Remeš, M.; Veselý, J. In α-Alkylation of Carbonyl Compounds, Stereoselective Organocatalysis, John Wiley & Sons, New York, 2013, p. 267. pmid: 28649462
	(f) Shibatomi, K.; Narayama, A. Asian J. Org. Chem. 2013, 2, 812. doi: 10.1002/ajoc.v2.10 pmid: 28649462
	(g) Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207. doi: 10.1021/acscatal.6b01886 pmid: 28649462
	(h) Cano, R.; Zakarian, A.; McGlacken, G. P. Angew. Chem., Int. Ed. 2017, 56, 9278. doi: 10.1002/anie.v56.32 pmid: 28649462
	(i) Afewerki, S.; Córdova, A. Top. Curr. Chem. 2019, 377, 38. pmid: 28649462
	(j) Hao, Y.-J.; Hu, X.-S.; Zhou, Y.; Zhou, J.; Yu, J.-S. ACS Catal. 2020, 10, 955. doi: 10.1021/acscatal.9b04480 pmid: 28649462
	(k) Lee, H.-E.; Kim, D.; You, A.; Park, M. H.; Kim, M.; Kim, C. Catalysts 2020, 10, 861. doi: 10.3390/catal10080861 pmid: 28649462
	(l) Escudero-Casao, M.; Licini, G.; Orlandi, M. Synlett 2021, 32, 1473. doi: 10.1055/a-1503-7339 pmid: 28649462
	(m) Wright, T. B.; Evans, P. A. Chem. Rev. 2021, 121, 9196. doi: 10.1021/acs.chemrev.0c00564 pmid: 28649462
	(n) Dong, S.; Liu, X.; Feng, X. Acc. Chem. Res. 2022, 55, 415. doi: 10.1021/acs.accounts.1c00664 pmid: 28649462
[4]	(a) Godard, C.; Perandones, B. F.; Gual, A.; Claver, C. In Asymmetric Carbonylations, Comprehensive Inorganic Chemistry II, 2nd ed., Elsevier, Amsterdam, 2013, p. 383.
	(b) Davison, R. T.; Kuker, E. L.; Dong, V. M. Acc. Chem. Res. 2021, 54, 1236. doi: 10.1021/acs.accounts.0c00771
	(c) Bai, S.-T.; Wen, J.; Zhang, X. In Asymmetric Carbonylations, Comprehensive Inorganic Chemistry II, 2nd ed., Elsevier, Amsterdam, 2022, p. 611.
[5]	(a) Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485. doi: 10.1021/cr00039a008
	(b) Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. A-Chem. 1995, 104, 17. doi: 10.1016/1381-1169(95)00130-1
	(c) Perandones, B. F.; Godard, C.; Claver, C. In Hydroformylation for Organic Synthesis, Springer, Berlin, 2013, p. 79.
	(d) Li, S.-L.; Li, Z.-X.; You, C.; Lv, H.; Zhang, X.-M. Chin. J. Org. Chem. 2019, 39, 1568 (in Chinese) doi: 10.6023/cjoc201903044
	(李帅龙, 李庄星, 由才, 吕辉, 张绪穆, 有机化学, 2019, 39, 1568.)
	(e) Chakrabortty, S.; Almasalma, A. A.; de Vries, J. G. Catal. Sci. Technol. 2021, 11, 5388. doi: 10.1039/D1CY00737H
	(f) Shen, C.; Dong, K. Synlett 2022, 33, 815. doi: 10.1055/a-1796-2255
[6]	(a) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. doi: 10.1038/nature13274 pmid: 32905517
	(b) Ananikov, V. P. ACS Catal. 2015, 5, 1964. doi: 10.1021/acscatal.5b00072 pmid: 32905517
	(c) Su, B.; Cao, Z.-C.; Shi, Z.-J. Acc. Chem. Res. 2015, 48, 886. doi: 10.1021/ar500345f pmid: 32905517
	(d) Choi, J.; Fu, G. C. Science 2017, 356, eaaf7230. doi: 10.1126/science.aaf7230 pmid: 32905517
	(e) Diccianni, J. B.; Diao, T. Trends Chem. 2019, 1, 830. doi: 10.1016/j.trechm.2019.08.004 pmid: 32905517
	(f) Ogoshi, S. Nickel Catalysis in Organic Synthesis: Methods and Reactions, John Wiley & Sons, New York, 2019. pmid: 32905517
	(g) Clevenger, A. L.; Stolley, R. M.; Aderibigbe, J.; Louie, J. Chem. Rev. 2020, 120, 6124. doi: 10.1021/acs.chemrev.9b00682 pmid: 32905517
	(h) Poremba, K. E.; Dibrell, S. E.; Reisman, S. E. ACS Catal. 2020, 10, 8237. doi: 10.1021/acscatal.0c01842 pmid: 32905517
	(i) Zhou, Z.; Xu, S.; Zhang, J.; Kong, W. Org. Chem. Front. 2020, 7, 3262. doi: 10.1039/D0QO00901F pmid: 32905517
	(j) Zhu, S.; Zhao, X.; Li, H.; Chu, L. Chem. Soc. Rev. 2021, 50, 10836. doi: 10.1039/D1CS00399B pmid: 32905517
[7]	(a) Ding, Z.; Wang, Y.; Liu, W.; Chen, Y.; Kong, W. J. Am. Chem. Soc. 2021, 143, 53. doi: 10.1021/jacs.0c10055
	(b) Chen, Z.-H.; Sun, R.-Z.; Yao, F.; Hu, X.-D.; Xiang, L.-X.; Cong, H.; Liu, W.-B. J. Am. Chem. Soc. 2022, 144, 4776. doi: 10.1021/jacs.2c01237
[8]	Hayashi, M.; Bachman, S.; Hashimoto, S.; Eichman, C. C.; Stoltz, B. M. J. Am. Chem. Soc. 2016, 138, 8997. doi: 10.1021/jacs.6b02120 pmid: 27373124
[9]	Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442. doi: 10.1021/ja402922w pmid: 23634932
[10]	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
[11]	Wu, J.; Wu, H.; Liu, X.; Zhang, Y.; Huang, G.; Zhang, C. Org. Lett. 2022, 24, 4322. doi: 10.1021/acs.orglett.2c01208
[12]	(a) Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522. doi: 10.1039/C5QO00437C
	(b) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 0052. doi: 10.1038/s41570-017-0052
	(c) Badir, S. O.; Molander, G. A. Chem 2020, 6, 1327. doi: 10.1016/j.chempr.2020.05.013
	(d) Zhang, H.-H.; Chen, H.; Zhu, C.; Yu, S. Sci. China: Chem. 2020, 63, 637. doi: 10.1007/s11426-019-9701-5
	(e) Zhu, C.; Yue, H.; Chu, L.; Rueping, M. Chem. Sci. 2020, 11, 4051. doi: 10.1039/D0SC00712A
	(f) Lu, F.-D.; He, G.-F.; Lu, L.-Q.; Xiao, W.-J. Green Chem. 2021, 23, 5379. doi: 10.1039/D1GC00993A
	(g) Lu, F.-D.; Chen, J.; Jiang, X.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2021, 50, 12808. doi: 10.1039/D1CS00210D
	(h) Chan, A. Y.; Perry, I. B.; Bissonnette, N. B.; Buksh, B. F.; Edwards, G. A.; Frye, L. I.; Garry, O. L.; Lavagnino, M. N.; Li, B. X.; Liang, Y.; Mao, E.; Millet, A.; Oakley, J. V.; Reed, N. L.; Sakai, H. A.; Seath, C. P.; MacMillan, D. W. C. Chem. Rev. 2022, 122, 1485. doi: 10.1021/acs.chemrev.1c00383
	(i) Zhu, S.; Li, H.; Li, Y.; Huang, Z.; Chu, L. Org. Chem. Front. 2022.
[13]	Gandolfo, E.; Tang, X.; Raha Roy, S.; Melchiorre, P. Angew. Chem., Int. Ed. 2019, 58, 16854. doi: 10.1002/anie.201910168 pmid: 31532568
[14]	Shu, X.; Huan, L.; Huang, Q.; Huo, H. J. Am. Chem. Soc. 2020, 142, 19058. doi: 10.1021/jacs.0c10471
[15]	Huan, L.; Shu, X.; Zu, W.; Zhong, D.; Huo, H. Nat. Commun. 2021, 12, 3536. doi: 10.1038/s41467-021-23887-2
[16]	Donets, P. A.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 11772. doi: 10.1021/ja406730t pmid: 23909575
[17]	(a) Chen, J.; Zhu, S. J. Am. Chem. Soc. 2021, 143, 14089. doi: 10.1021/jacs.1c07851
	(b) Chen, J.; Deng, G.; Wang, Y.; Zhu, S. Chin. J. Chem. 2023, 41, 294. doi: 10.1002/cjoc.v41.3
[18]	Jiang, X.; Sheng, F.-T.; Zhang, Y.; Deng, G.; Zhu, S. J. Am. Chem. Soc. 2022, 144, 21448. doi: 10.1021/jacs.2c10785
[19]	(a) Derosa, J.; Apolinar, O.; Kang, T.; Tran, V. T.; Engle, K. M. Chem. Sci. 2020, 11, 4287. doi: 10.1039/C9SC06006E
	(b) Luo, Y.-C.; Xu, C.; Zhang, X. Chin. J. Chem. 2020, 38, 1371. doi: 10.1002/cjoc.v38.11
	(c) Qi, X.; Diao, T. ACS Catal. 2020, 10, 8542. doi: 10.1021/acscatal.0c02115
	(d) Tu, H.-Y.; Zhu, S.; Qing, F.-L.; Chu, L. Synthesis 2020, 52, 1346. doi: 10.1055/s-0039-1690842
	(e) Xu, L.; Wang, F.; Chen, F.; Zhu, S.-Q.; Chu, L.-L. Chin. J. Org. Chem. 2022, 42, 1. (in Chinese) doi: 10.6023/cjoc202109002
	(徐磊, 王方, 陈凡, 朱圣卿, 储玲玲, 有机化学, 2022, 42, 1.) doi: 10.6023/cjoc202109002
[20]	Li, Y.; Zhang, F.-P.; Wang, R.-H.; Qi, S.-L.; Luan, Y.-X.; Ye, M. J. Am. Chem. Soc. 2020, 142, 19844. doi: 10.1021/jacs.0c09949
[21]	He, F.; Hou, L.; Wu, X.; Ding, H.; Qu, J.; Chen, Y. CCS Chem. 2023, 5, 341. doi: 10.31635/ccschem.022.202202010
[22]	Lan, Y.; Wang, C. Commun. Chem. 2020, 3, 45. doi: 10.1038/s42004-020-0292-3
[23]	Wu, J.; Wang, C. Org. Lett. 2021, 23, 6407. doi: 10.1021/acs.orglett.1c02223
[24]	Wu, X.; Qu, J.; Chen, Y. J. Am. Chem. Soc. 2020, 142, 15654. doi: 10.1021/jacs.0c07126
[25]	Wu, X.; Luan, B.; Zhao, W.; He, F.; X.-Y. Wu, J. Qu, Y. Chen, Angew. Chem., Int. Ed. 2022, 61, e202111598.
[26]	Wu, X.; Turlik, A.; Luan, B.; He, F.; Qu, J.; Houk, K. N.; Chen, Y. Angew. Chem., Int. Ed. 2022, 61, e202207536.
[27]	Zhang, C.; Wu, X.; Xia, T.; Qu, J.; Chen, Y. Nat. Commun. 2022, 13, 5964. doi: 10.1038/s41467-022-33425-3
[28]	Fan, P.; Lan, Y.; Zhang, C.; Wang, C. J. Am. Chem. Soc. 2020, 142, 2180. doi: 10.1021/jacs.9b12554
[29]	Marchese, A. D.; Larin, E. M.; Mirabi, B.; Lautens, M. Acc. Chem. Res. 2020, 53, 1605. doi: 10.1021/acs.accounts.0c00297
[30]	Marchese, A. D.; Wollenburg, M.; Mirabi, B.; Abel-Snape, X.; Whyte, A.; Glorius, F.; Lautens, M. ACS Catal. 2020, 10, 4780. doi: 10.1021/acscatal.0c00841