导向基辅助的过渡金属催化C(sp3)—H键氮宾插入反应研究进展

doi:10.6023/cjoc202211041

摘要/Abstract

过渡金属催化C(sp³)—H键活化形成碳-氮键的反应一直是具有挑战性且热门的研究领域. 过渡金属催化的C(sp³)—H胺化策略为形成C—N键提供了更为直接高效的方式. 随着碳-氢键活化领域的蓬勃发展, 人们发展出了丰富多样的导向基和过渡金属催化体系, 为通过内轨机制实现C(sp³)—H胺化提供了有效工具. 近年来, 导向基辅助的C(sp³)—H键胺化反应取得了重要进展, 许多基于不同过渡金属的催化体系和廉价高效的胺化试剂得以开发. 综述了近十年来在导向基团辅助下, 过渡金属催化C(sp³)—H氮宾插入反应的研究进展.

关键词: 导向基, 氮宾插入, 过渡金属, C(sp³)—H, 碳-氮键形成

The transition metal catalyzed activation of C(sp³)—H bonds to form carbon-nitrogen bonds has been a challenging and hot research area. The transition metal-catalyzed C(sp³)—H amination strategy provides a more direct and efficient way to form C—N bonds. With the vigorous development in the field of C—H bond activation, a variety of directing groups and transition metal catalyst systems have been developed, which provide effective tools for C(sp³)—H amination through the inner sphere mechanism. In recent years, important progress has been made in directing group-assisted C(sp³)—H bond amination reactions, and many catalyst systems based on different transition metals with cheap and efficient amination reagents have been developed. The research progress of transition metal-catalyzed C(sp³)—H nitrene insertion reaction assisted by directing groups in the past decade is reviewed.

Key words: directing group, nitrene insertion, transition metal, C(sp³)—H, C—N bond formation

引用此文

杨幸, 刘旭, 王丽佳. 导向基辅助的过渡金属催化C(sp³)—H键氮宾插入反应研究进展[J]. 有机化学, 2023, 43(3): 914-923.

Xing Yang, Xu Liu, Lijia Wang. Recent Progress in Transition Metal Catalyzed C(sp³)—H Nitrene Insertion Reactions Assisted by Directing Groups[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 914-923.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 23

图式1. 过渡金属催化的C(sp3)—H胺化反应的机制类型

Scheme 1. Mechanism types of transition metal-catalyzed C(sp3)—H amination reactions

图式2. 肟醚导向的铑催化C(sp3)–H胺化反应

Scheme 2. Rhodium-catalyzed C(sp3)–H amination directed by oxime

图式3. 肟醚导向的铱催化C(sp3)—H胺化反应

Scheme 3. Iridium-catalyzed C(sp3)—H amination directed by oxime

图式4. 喹啉导向的钴催化C(sp3)—H胺化反应

Scheme 4. Cobalt-catalyzed C(sp3)—H amination directed by quinolone

图式5. 喹啉导向的铑催化不对称C(sp3)—H胺化反应

Scheme 5. Rhodium-catalyzed asymmetric C(sp3)—H amination directed by quinoline

图式6. 吡啶导向的铑催化不对称C(sp3)—H胺化反应

Scheme 6. Rhodium-catalyzed asymmetric C(sp3)—H amination directed by pyridine

图式7. 硫代酰胺导向的钴催化C(sp3)—H胺化反应

Scheme 7. Cobalt-catalyzed C(sp3)—H amination directed by thioamides

图式8. 硫代酰胺导向的钴催化不对称C(sp3)—H胺化反应

Scheme 8. Cobalt-catalyzed asymmetric C(sp3)—H amination directed by thioamides

图式9. 二噻烷导向的铑催化C(sp3)—H胺化反应

Scheme 9. Rhodium-catalyzed C(sp3)—H amination directed by dithiane

图式10. 咪唑酰胺导向的铱催化C(sp3)—H胺化反应

Scheme 10. Iridium-catalyzed C(sp3)—H amination directed by 2-acylimidazoles

图式11. 硫醚导向的镍催化C(sp3)—H胺化反应

Scheme 11. Ni-catalyzed C(sp3)—H amination directed by thioether

图式12. TsN3参与肟醚导向铱催化C(sp3)—H胺化反应

Scheme 12. Iridium-catalyzed C(sp3)—H amination involving TsN3 directed by oxime

图式13. TrocN3参与肟醚导向的铱催化C(sp3)—H胺化反应

Scheme 13. Iridium-catalyzed C(sp3)—H amination involving TrocN3 directed by oxime

图式14. 吡啶导向的铑/铱催化C(sp3)—H胺化反应

Scheme 14. Rhodium/iridium-catalyzed C(sp3)—H amination directed by pyridine

图式15. 喹啉酰胺导向镍催化C(sp3)—H胺化反应

Scheme 15. Ni-catalyzed C(sp3)—H amination directed by quinoline-amide

图式16. 吡啶酰胺促进的铱催化的碳-氢键胺化反应

Scheme 16. Iridium-catalyzed C(sp3)–H amination promoted by pyridine-amide

图式17. 吡啶导向的铑催化C(sp3)—H胺化反应

Scheme 17. Rhodium-catalyzed C(sp3)—H amination directed by pyridine

图式18. 肟醚导向的铑催化不对称C(sp3)—H胺化反应

Scheme 18. Rhodium-catalyzed asymmetric C(sp3)—H amination directed by oxime

图式19. 吡唑酰胺导向的铑催化C(sp3)—H胺化反应

Scheme 19. Rhodium-catalyzed C(sp3)—H amination directed by pyrazole-amide

图式20. 肟醚导向的钯催化C(sp3)—H胺化反应

Scheme 20. Palladium-catalyzed C(sp3)—H amination directed by oxime

图式21. 吡啶导向的铑催化C(sp3)—H胺化反应

Scheme 21. Rhodium-catalyzed C(sp3)—H amination directed by pyridine

图式22. 氨茴内酐参与的吡啶导向的铑催化C(sp3)—H胺化反应

Scheme 22. Rhodium-catalyzed C(sp3)—H amination directed by pyridine with anthranils

图式23. 氨茴内酐参与的硫代酰胺导向的钴催化C(sp3)—H胺化反应

Scheme 23. Cobalt-catalyzed C(sp3)—H amination directed by thioamide involving anthranils

参考文献 28

[1]	Ricci, A. Amino Group Chemistry: From Synthesis to the Life Sciences, Wiley-VCH, Weinheim, 2008.
[2]	(a) Zhao, J.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235. (in Chinese) doi: 10.6023/A15010063
	(赵金钵, 张前, 化学学报, 2015, 73, 1235.) doi: 10.6023/A15010063
	(b) Li, J.; Zhang, Y. Nat. Rev. Chem. 2022, 6, 303. doi: 10.1038/s41570-022-00379-5
	(c) Ma, J.-L.; Zhou, X.-M.; Guo, P.-H.; Cheng, H.-C.; Ji, H.-B. Chin. J. Chem. 2022, 40, 1204. doi: 10.1002/cjoc.v40.10
	(d) Saranya, P. V.; Neetha, M.; Philip, R. M. Tetrahedron 2022, 104, 132582. doi: 10.1016/j.tet.2021.132582
	(e) Hwang, H.; Kim, J.; Jeong, J.; Chang, S. J. Am. Chem. Soc. 2014, 136, 10770. doi: 10.1021/ja5053768
[3]	(a) Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417. doi: 10.1038/nature06485 pmid: 32995499
	(b) Davies, H. M. L.; Liao, K.-B. Nat. Rev. Chem. 2019, 3, 347. doi: 10.1038/s41570-019-0099-x pmid: 32995499
	(c) Du, B.; Chan, C.-M.; Au, C.-M.; Yu, W.-Y. Acc. Chem. Res. 2022, 55, 2123. doi: 10.1021/acs.accounts.2c00283 pmid: 32995499
	(d) Liang, H.; Wang, J. Chem.-Eur. J. 2022, 28, e202202461. pmid: 32995499
[4]	For review: (a) Godula, K.; Sames, D., Science 2006, 312, 67. pmid: 21500412
	(b) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439. doi: 10.1016/j.tet.2005.11.027 pmid: 21500412
	(c) Zalatan, D. N.; Du Bois, J. Top. Curr. Chem. 2010, 292, 347. pmid: 21500412
	(d) Driver, T. G. Org. Biomol. Chem. 2010, 8, 3831. doi: 10.1039/c005219c pmid: 21500412
	For leading references: pmid: 21500412
	(e) Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124. doi: 10.1021/ja312277g pmid: 21500412
	(f) He, J.; Wasa, M.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 3387. doi: 10.1021/ja400648w pmid: 21500412
	(g) Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135. doi: 10.1021/ja406484v pmid: 21500412
	(h) Shan, G.; Yang, X.; Zong, Y.; Rao, Y. Angew. Chem., Int. Ed. 2013, 52, 13606. doi: 10.1002/anie.201307090 pmid: 21500412
	(i) Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906. doi: 10.1039/c3sc51747k pmid: 21500412
	(j) Rodríguez, N.; Romero-Revilla, J. A.; Fernández-Ibáñez, M. Á.; Carretero, J. C. Chem. Sci. 2013, 4, 175. doi: 10.1039/C2SC21162A pmid: 21500412
	(k) Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898. doi: 10.1021/ja411715v pmid: 21500412
	(l) Wu, X.; Zhao, Y.; Ge, H. J. Am. Chem. Soc. 2014, 136, 1789 doi: 10.1021/ja413131m pmid: 21500412
[5]	Wang, H.; Tang, G.; Li, X. Angew. Chem., Int. Ed. 2015, 54, 13049. doi: 10.1002/anie.201506323 pmid: 26480337
[6]	Dong, Y.; Chen, J.; Xu, H. Chem. Commun. 2018, 54, 11096. doi: 10.1039/C8CC05637D
[7]	Antien, K.; Geraci, A.; Parmentier, M.; Baudoin, O. Angew. Chem., Int. Ed. 2021, 60, 22948. doi: 10.1002/anie.v60.42
[8]	Barsu, N.; Rahman, M. A.; Sen, M.; Sundararaju, B. Chem.-Eur. J. 2016, 22, 9135. doi: 10.1002/chem.201601597
[9]	Fukagawa, S.; Kojima, M.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2019, 58, 18154. doi: 10.1002/anie.201911268 pmid: 31593365
[10]	Kato, Y.; Lin, L.; Kojima, M.; Yoshino, T.; Matsunaga, S. ACS Catal. 2021, 11, 4271. doi: 10.1021/acscatal.1c00765
[11]	Tan, P. W.; Mak, A. M.; Sullivan, M. B.; Dixon, D. J.; Seayad, J. Angew. Chem., Int. Ed. 2017, 56, 16550. doi: 10.1002/anie.201709273
[12]	Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; Yoshino, T.; Matsunaga, S. Angew. Chem., Int. Ed. 2019, 58, 1153. doi: 10.1002/anie.201812215 pmid: 30478868
[13]	Sekine, D.; Ikeda, K.; Fukagawa, S.; Kojima, M.; Yoshino, T.; Matsunaga, S. Organometallics 2019, 38, 3921. doi: 10.1021/acs.organomet.9b00407
[14]	Shi, H.; Dixon, D. J. Chem. Sci. 2019, 10, 3733. doi: 10.1039/C8SC05225E
[15]	Mahato, S. K.; Ohara, N.; Khake, S. M.; Chatani, N. I. ACS Catal. 2021, 11, 7126. doi: 10.1021/acscatal.1c01901
[16]	Du, B.; Ouyang, Y.; Chen, Q.; Yu, W.-Y. J. Am. Chem. Soc. 2021, 143, 14962 doi: 10.1021/jacs.1c05834
[17]	Kang, T.; Kim, Y.; Lee, D.; Wang, Z.; Chang, S. J. Am. Chem. Soc. 2014, 136, 4141. doi: 10.1021/ja501014b
[18]	Zhang, T.; Hu, X.; Dong, X.; Li, G.; Lu, H. Org. Lett. 2018, 20, 6260. doi: 10.1021/acs.orglett.8b02738 pmid: 30232895
[19]	Han, J.-L.; Qin, Y.; Zhao, D. ACS Catal. 2019, 9, 6020. doi: 10.1021/acscatal.9b00771
[20]	Kim, Y. B.; Won, J.; Lee, J.; Kim, J.; Zhou, B.; Park, J.-W.; Baik, M.-H.; Chang, S. ACS Catal. 2021, 11, 3067. doi: 10.1021/acscatal.1c00070
[21]	Xiao, X.; Hou, C.; Zhang, Z.; Ke, Z.; Lan, J.; Jiang, H.; Zeng, W. Angew. Chem., Int. Ed. 2016, 55, 11897. doi: 10.1002/anie.v55.39
[22]	Huang, X.; Wang, Y.; Lan, J.; You, J. Angew. Chem., nt. Ed. 2015, 54, 9404.
[23]	Liu, B.; Xie, P.; Zhao, J.; Wang, J.; Wang, M.; Jiang, Y.; Chang, J.; Li, X. Angew. Chem., Int. Ed. 2021, 60, 8396. doi: 10.1002/anie.v60.15
[24]	Wang, Y.; Liu, H.; Li, B.; Wang, B. Adv. Synth. Catal. 2019, 361, 1564. doi: 10.1002/adsc.v361.7
[25]	Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048. doi: 10.1021/ja062856v
[26]	Yu, S.; Tang, G.; Li, Y.; Zhou, X.; Lan, Y.; Li, X. Angew. Chem., Int. Ed. 2016, 55, 8696. doi: 10.1002/anie.201602224
[27]	Tang, C.; Zou, M.; Liu, J.; Wen, X.; Sun, X.; Zhang, Y.; Jiao, N. Chem.-Eur. J. 2016, 22, 11165. doi: 10.1002/chem.201602556
[28]	Liu, R.-H.; Shan, Q.-C.; Hu, X.-H.; Loh, T.-P. Chem. Commun. 2019, 55, 5519. doi: 10.1039/C9CC01715A

导向基辅助的过渡金属催化C(sp³)—H键氮宾插入反应研究进展

Recent Progress in Transition Metal Catalyzed C(sp³)—H Nitrene Insertion Reactions Assisted by Directing Groups

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 23

参考文献 28

相关文章 15

编辑推荐

相关统计

本文评价

[1]	付雅彤, 孙超凡, 张丹, 金成国, 陆居有. 巢式-碳硼烷硼氢键官能化反应研究进展[J]. 有机化学, 2024, 44(2): 438-447.
[2]	刘杰, 韩峰, 李双艳, 陈天煜, 陈建辉, 徐清. 无过渡金属参与甲基杂环化合物与醇的选择性有氧烯基化反应[J]. 有机化学, 2024, 44(2): 573-583.
[3]	赵红琼, 于淼, 宋冬雪, 贾琦, 刘颖杰, 季宇彬, 许颖. 羧酸脱羧羟基化反应研究进展[J]. 有机化学, 2024, 44(1): 70-84.
[4]	董江湖, 宣良明, 王池, 赵晨熙, 王海峰, 严琼姣, 汪伟, 陈芬儿. 无过渡金属或无光催化剂条件下可见光促进喹喔啉酮C(3)—H官能团化研究进展[J]. 有机化学, 2024, 44(1): 111-136.
[5]	王文芳. 过渡金属催化不对称C—H硼化反应研究进展[J]. 有机化学, 2023, 43(9): 3146-3166.
[6]	高晓阳, 翟锐锐, 陈训, 王烁今. 碳酸亚乙烯酯参与C—H键活化反应的研究进展[J]. 有机化学, 2023, 43(9): 3119-3134.
[7]	王灵娜, 刘晓庆, 林钢, 金泓颖, 焦民均, 刘雪粉, 罗书平. 光促进双(4-二苯甲酮)苯醚催化C(sp³)—H键活化构建C—S键[J]. 有机化学, 2023, 43(8): 2848-2854.
[8]	陈新强, 张敬. 伯醇的脱羟甲基反应的研究进展[J]. 有机化学, 2023, 43(8): 2711-2719.
[9]	董思凡, 李昊龙, 秦源, 范士明, 刘守信. 氨基酸作为瞬态导向基在碳氢键活化反应中的研究进展[J]. 有机化学, 2023, 43(7): 2351-2367.
[10]	石义军, 孙馨悦, 曹晗, 别福升, 马杰, 刘哲, 丛兴顺. 室温下酯与伯硫醇的硫酯化反应[J]. 有机化学, 2023, 43(7): 2499-2505.
[11]	徐忠荣, 万结平, 刘云云. 基于热、光以及电化学过程的无过渡金属碳-氢键硫氰化和硒氰化反应[J]. 有机化学, 2023, 43(7): 2425-2446.
[12]	户晓兢, 郭斐翔, 朱润青, 周柄棋, 张涛, 房立真. 对烷氧基酚的合成及其去芳构化后的合成应用[J]. 有机化学, 2023, 43(6): 2239-2244.
[13]	秦娇, 陈杰, 苏艳. 无过渡金属催化的α-溴代茚酮自由基裂解反应合成(2-氰基苯基)乙酸-2,2,6,6-四甲基哌啶酯[J]. 有机化学, 2023, 43(6): 2171-2177.
[14]	徐光利, 许静, 徐海东, 崔香, 舒兴中. 过渡金属催化烯烃和炔烃合成1,3-共轭二烯化合物研究进展[J]. 有机化学, 2023, 43(6): 1899-1933.
[15]	褚杨杨, 韩召斌, 丁奎岭. 动力学拆分在过渡金属催化的不对称(转移)氢化中的应用研究[J]. 有机化学, 2023, 43(6): 1934-1951.