可见光驱动基团迁移引发的烯烃双官能团化反应

doi:10.6023/cjoc202207037

摘要/Abstract

烯烃的双官能团化反应作为有机化学研究的重要合成手段, 在合成化学领域扮演着重要的角色. 近年来, 自由基参与分子内官能团迁移引发的烯烃双官能团化反应迅速崛起, 为烯烃的双官能化反应提供了新思路. 该策略具有原子经济性好和环境友好性等优点. 温和、绿色的光催化作为产生自由基前体的有效手段, 激发了化学家们利用光催化驱动基团迁移引发烯烃双官能团化反应的兴趣. 根据光催化自由基参与的近/远端芳基、杂芳基、亚胺、氰基、酰基、炔基和烯基等官能团迁移的种类, 对烯烃双官能团化反应进行归类总结, 并对部分反应机理进行了论述.

关键词: 可见光催化, 自由基, 迁移, 烯烃, 双官能团化

As an important synthetic method in organic chemistry research, the difunctionalization of alkenes plays an important role in the field of synthetic chemistry. In recent years, the difunctionalization of alkenes caused by free radicals participating in the migration of intramolecular functional groups has risen rapidly, providing a new idea for the difunctionalization of alkenes. This strategy has the advantages of atom economy and environmental friendliness. As an effective means to generate radical precursors, mild and green photocatalysis has inspired chemistsʼ interest in initiating difunctionalization of alkenes by using photocatalysis to drive group migration. According to the species of near and far aryl, heteroaryl, imine, cyano, acyl, alkynyl, alkenyl and other functional groups involved in photocatalytic radicals, the alkene difunctionalization reactions are classified and summarized, and some reaction mechanisms are discussed.

Key words: visible-light photoredox, radical, migration, alkene, difunctionalization

引用此文

李猛, 赵冬阳, 孙凯. 可见光驱动基团迁移引发的烯烃双官能团化反应[J]. 有机化学, 2022, 42(12): 4152-4168.

Meng Li, Dongyang Zhao, Kai Sun. Visible Light Driving Alkene Difunctionalization Reaction Involving Group Migration[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4152-4168.

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

分享此文

图/表 38

图式1. 蓝光LED照射下构建具有季碳结构的胺类化合物

Scheme 1. Construction of amine compounds with quaternary carbon structures under blue LED

图式2. 在可见光照射下构建苯并呋喃类化合物

Scheme 2. Construction of benzofuran compounds under visible light

图式3. 蓝光LED照射下构建α-芳基-β-烷基酮

Scheme 3. Construction of α-aryl-β-alkyl ketones under blue LED

图式4. 可见光照射下构建1,5-二羰基化合物

Scheme 4. Construction of the 1,5-dicarbonyl compounds under visible light

图式5. 蓝光照射下构建二氟-1,5-二羰基化合物

Scheme 5. Construction of the difluoro 1,5-dicarbonyl compounds under blue LEDs

图式6. 蓝光LED照射下构建β-芳基-γ-酮氧化膦

Scheme 6. Construction of β-aryl-γ-ketophosphine oxides under blue LED

图式7. 蓝光LED照射下构建α-芳基-γ-甲基亚砜基酮

Scheme 7. Construction of α-aryl-γ-methylsulfinyl ketones under blue LED

图式8. 蓝光LED照射下构建β-三氟甲基-α-芳基酮

Scheme 8. Construction of β-trifluoromethyl-α-aryl ketones under blue LED

图式9. 蓝光LED照射下构建β-三氟甲基-α-芳基酮

Scheme 9. Construction of β-trifluoromethyl-α-aryl ketones under blue LED

图式10. 蓝光LED照射下合成γ-氰基酮

Scheme 10. Construction of γ-cyano ketones under blue LED

图式11. 蓝光LED照射下合成γ-羰基膦酸酯

Scheme 11. Construction of γ-oxo-phosphonate under blue LED

图式12. 蓝光LED照射下构建1,5-二酮

Scheme 12. Construction of 1,5-diketones under blue LED

图式13. 蓝光LED照射下构建β-二氟甲基-α-芳基酮

Scheme 13. Construction of β-drifluoromethyl-α-aryl ketones under blue LED

图式14. 蓝光LED照射下构建全氟烷基化合物

Scheme 14. Construction of perfluoroalkylated compounds under blue LED

图式15. 可见光照射下构建环酮类化合物

Scheme 15. Construction of the cyclic ketones under visible light

图式16. 可见光照射下构建1,4-二羰基化合物

Scheme 16. Construction of 1,4-dicarbonyl compounds under visible light

图式17. 蓝光LED照射下构建二氟甲基化环戊酮

Scheme 17. Construction of difluoromethylated cyclopentanone under blue LED

图式18. 蓝光LED照射下构建β-磺化环戊酮

Scheme 18. Construction of β-sulfonated cyclopentanones under blue LEDs

图式19. 蓝光LED照射下合成β-二氟化-α-吡啶酮

Scheme 19. Construction of β-difluorinated-α-pyridone under blue LED

图式20. 蓝光LED照射下构建1,2-二硼酸酯

Scheme 20. Construction of 1,2-diboronic esters under blue LED

图式21. 可见光照射下构建α-芳基-β-三氟甲基酰胺/含CF3的吲哚/异喹啉二酮

Scheme 21. Construction of α-aryl-β-trifluor-omethyl amides and CF3-containing oxindoles/isoquinolinediones under visible light

图式22. 可见光照射下构建α-芳基-β-三氟甲基酰胺

Scheme 22. Construction of α-aryl-β-trifluoromethylamides under visible light

图式23. 可见光照射下构建全氟取代的吲哚或α-芳基-β-氟烷基酰胺

Scheme 23. Construction of perfluorinated indoles or α-aryl- β-fluoroalkylamides under visible light

图式24. 可见光照射下构建α-三氟甲基化酮类化合物

Scheme 24. Construction of α-trifluoromethylated ketones under visible light

图式25. 蓝光LED照射下构建二氟烷基化四环化合物

Scheme 25. Construction of difluoroalkylated tetracycles under blue LED

图式26. 蓝光LED照射下构建2,2-二芳基乙胺类化合物

Scheme 26. Construction of 2,2-diarylethylamine compounds under blue LED

图式27. 蓝光LED照射下构建二氟烷基化苯并噻唑类化合物

Scheme 27. Construction of difluoroalkylated benzothiazoles under blue LED

图式28. 可见光照射下构建二氟酯基酰胺类化合物

Scheme 28. Construction of difluoroester amides under visible light

图式29. 可见光照射下构建二氟和单氟烷基酮

Scheme 29. Construction of di-/mono-fluorinated alkyl ketones under visible light

图式30. 蓝光LED照射下构建二氟烷基化炔酮

Scheme 30. Construction of difluoroalkylated alkynyl ketones under blue LED

图式31. 蓝光LED照射下构建苯并噻唑酮

Scheme 31. Construction of benzothiazolones under blue LED

图式32. 蓝光照射下构建杂芳基和肟基取代的烷基砜类化合物

Scheme 32. Construction of heteroaryl- and oximino-substituted alkyl sulfones under blue LEDs

图式33. 可见光照射下构建环戊烷羧酸盐

Scheme 33. Construction of cyclopentane carboxylates under visible light

图式34. 可见光照射下构建环己烯

Scheme 34. Construction of cyclohexene under visible light

图式35. 蓝光LED照射下构建二氟和单氟烷基腈

Scheme 35. Construction of di- and mono-fluorinated alkyl nitriles under blue LED

图式36. 蓝光LED照射下构建全氟烷基化酮类化合物

Scheme 36. Construction of perfluoroalkylated ketones under blue LED

图式37. 可见光照射下构建亚胺醇

Scheme 37. Construction of imino alcohols under visible light

图式38. 可见光照射下构建二氟烷基化/膦酰化α,α-二芳基烷基脲

Scheme 38. Construction of difluoroalkylated/phosphonylated α,α-diarylalkylureas under visible light

参考文献 45

[1]	(a) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271. doi: 10.1021/cr950010w pmid: 11749272
	(b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. doi: 10.1016/S0040-4020(97)10427-6 pmid: 11749272
	(c) Baird, M. C. Chem. Rev. 2000, 100, 1471. pmid: 11749272
	(d) Takacs, J. M.; Jiang, X.-T. Curr. Org. Chem. 2003, 7, 369. doi: 10.2174/1385272033372851 pmid: 11749272
	(e) Prunet, J. Angew. Chem., nt. Ed. 2003, 42, 2826. pmid: 11749272
	(f) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., nt. Ed. 2004, 43, 3368. pmid: 11749272
	(g) Zhang, Z.; Yan, J.; Ma, D.; Sun, J. Chin. Chem. Lett. 2019, 30, 1509. doi: 10.1016/j.cclet.2019.04.023 pmid: 11749272
	(h) Wang, X.; Lei, J.; Liu, Y.-J.; Ye, Y.; Li, J.-Z.; Sun, K. Org. Chem. Front. 2021, 8, 2079. doi: 10.1039/D0QO01629B pmid: 11749272
[2]	(a) Liu, G.; Shannon, S. S. Chem. Rev. 2011, 111, 2981. doi: 10.1021/cr100371y
	(b) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; Kojer, H. Angew. Chem., nt. Ed. 1959, 71, 176.
	(c) Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, A. Angew. Chem., nt. Ed. 1962, 1, 80.
	(d) Jira, R. Angew. Chem., nt. Ed. 2009, 48, 9034.
[3]	(a) Liu, T.; Liu, J.; He, J.; Hong, Y.; Zhou, H.; Liu, Y-L.; Tang, S. Synthesis 2022, 54, 1919. doi: 10.1055/s-0040-1719900 pmid: 26580021
	(b) Wang, S.-W.; Yu, J.; Zhou, Q.-Y.; Chen, S.-Y.; Xu, Z.-H.; Tang, S. ACS Sustainable Chem. Eng. 2019, 7, 10154. doi: 10.1021/acssuschemeng.9b02178 pmid: 26580021
	(c) Yuan, L.; Jiang, S.-M.; Li, Z.-Z.; Zhu, Y.; Yu, J.; Li, L.; Li, M.-Z.; Tang, S.; Sheng, R.-R. Org. Biomol. Chem. 2018, 16, 2406. doi: 10.1039/C8OB00132D pmid: 26580021
	(d) Tang, S.; Yuan, L.; Deng, Y.-L.; Li, Z.-Z.; Wang, L.-N.; Huang, G.-X.; Sheng, R.-L. Tetrahedron Lett. 2017, 58, 329. doi: 10.1016/j.tetlet.2016.12.027 pmid: 26580021
	(e) Tang, S.; Yuan, L.; Li, Z.-Z.; Peng, Z.-Y.; Deng, Y.-L.; Wang, L.-N.; Huang, G.-X.; Sheng, R.-L. Tetrahedron Lett. 2017, 58, 2127. pmid: 26580021
	(f) Tang, S.; Deng, Y.-L.; Li, J.; Wang, W.-X.; Ding, G.-L.; Wang, M.-W.; Xiao, Z.-P.; Wang, Y.-C.; Sheng, R.-L. J. Org. Chem. 2015, 80, 12599. doi: 10.1021/acs.joc.5b01803 pmid: 26580021
[4]	(a) Xing, Y.; Li, C.; Meng, J.; Zhang, Z.; Wang, X.; Wang, Z.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3913. doi: 10.1002/adsc.202100446
	(b) Chen, N.; Lei, J.; Wang, Z.-C.; Liu, Y.-J.; Sun, K.; Tang, S. Chin. J. Org. Chem. 2022, 42, 1061. (in Chinese) doi: 10.6023/cjoc202109033
	( 陈宁, 雷佳, 王智传, 刘颖杰, 孙凯, 唐石, 有机化学, 2022, 42, 1061.) doi: 10.6023/cjoc202109033
	(c) Wang, X.; Zhang, Y.; Sun, K.; Meng, J.-P.; Zhang, B. Chin. J. Org. Chem. 2022, 41, 4588. (in Chinese) doi: 10.6023/cjoc202109046
	( 王薪, 张艳, 孙凯, 孟建萍, 张冰, 有机化学, 2021, 41, 4588.) doi: 10.6023/cjoc202109046
	(d) Guo, S.; Wang, X.; Zhao, D.; Zhang, Z.; Zhang, G.; Tang, S.; Sun, K. Asian J. Org. Chem. 2022, 11, e202100812.
	(e) Wang, X.; Meng, J.; Zhao, D.; Tang, S.; Sun, K. Chin. Chem. Lett. 2022, DOI: 10.1016/j.cclet.2022.08.016. doi: 10.1016/j.cclet.2022.08.016
[5]	(a) Wu, Z.; Ren, R.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, 10821. doi: 10.1002/anie.201605130
	(b) Wu, Z.; Wang, D.; Liu, Y.; Huang, L.; Zhu, C. J. Am. Chem. Soc. 2017, 139, 1388. doi: 10.1021/jacs.6b11234
	(c) Xu, Y.; Wu, Z.; Jiang, J.; Ke, Z.; Zhu, C. Angew. Chem., Int. Ed. 2017, 56, 4545. doi: 10.1002/anie.201700413
[6]	Stateman, L. M.; Nakafuku, K. M.; Nagib, D. A. Synthesis 2018, 50, 1569. doi: 10.1055/s-0036-1591930
[7]	Zhang, X.-M.; Tu, Y.-Q.; Zhang, F.-M.; Chen, Z.-H.; Wang, S.-H. Chem. Soc. Rev. 2017, 46, 2272. doi: 10.1039/C6CS00935B
[8]	Meng, Q.-Y.; Lei, T.; Zhao, L.-M.; Wu, C.-J.; Zhong, J.-J.; Gao, X.-W.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2014, 16, 5968. doi: 10.1021/ol502995h
[9]	Borra, S.; Chandrasekhar, D.; Khound, S.; Maurya, R. A. Org. Lett. 2017, 19, 5364. doi: 10.1021/acs.orglett.7b02643
[10]	Huang, H.-L.; Yan, H.; Yang, C.; Xia, W. Chem. Commun. 2015, 51, 4910. doi: 10.1039/C4CC10321A
[11]	Li, Y.; Liu, B.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2015, 2, 1457. doi: 10.1039/C5QO00220F
[12]	(a) Xu, P.; Hu, K.; Gu, Z.; Cheng, Y.; Zhu, C.-J. Chem. Commun. 2015, 51, 7222. doi: 10.1039/C5CC01189B
	(b) Wang, X.; Lei, J.; Liu, Y.; Ye, Y.; Li, J.; Sun, K. Org. Chem. Front. 2021, 8, 2079. doi: 10.1039/D0QO01629B
[13]	Yin, Y.; Weng, W.-Z.; Sun, J.-G.; Zhang, B. Org. Biomol. Chem. 2018, 16, 2356. doi: 10.1039/C8OB00231B
[14]	Lu, M.; Qin, H.; Lin, Z.; Huang, M.; Weng, W.; Cai, S. Org. Lett. 2018, 20, 7611. doi: 10.1021/acs.orglett.8b03340
[15]	Cai, S.; Tian, Y.; Zhang, J.; Liu, Z.; Lu, M.; Weng, W.; Huang, M. Adv. Synth. Catal. 2018, 360, 4084. doi: 10.1002/adsc.201800726
[16]	Wang, H.; Xu, Q.; Yu, S. Org. Chem. Front. 2018, 5, 2224. doi: 10.1039/C8QO00430G
[17]	Wang, Q.-L.; Chen, Z.; Zhou, C.-S.; Xiong, B.-Q.; Zhang, P.-L.; Yang, C.-A.; Liu, Y.; Zhou, Q. Tetrahedron Lett. 2018, 59, 4551. doi: 10.1016/j.tetlet.2018.11.025
[18]	Wang, C.; Huang, X.; Liu, X.; Gao, S.; Zhao, B.; Yang, S. Chin. Chem. Lett. 2020, 31, 677. doi: 10.1016/j.cclet.2019.08.011
[19]	Lin, Z.; Lu, M.; Liu, B.; Gao, J.; Huang, M.; Gan, Z.; Cai, S. New J. Chem. 2020, 44, 16031. doi: 10.1039/D0NJ03733H
[20]	Zhang, Y.; Ren, Z.; Liu, Y.-L.; Wang, Z.; Li, Z. Eur. J. Org. Chem. 2020, 2020, 5192. doi: 10.1002/ejoc.202000782
[21]	Li, Z.; Wang, M.; Shi, Z. Angew. Chem., Int. Ed. 2021, 60, 186. doi: 10.1002/anie.202010839
[22]	Kwon, S. J.; Kim, D. Y. Org. Lett. 2016, 18, 4562. doi: 10.1021/acs.orglett.6b02201 pmid: 27571287
[23]	Zhang, J.-J.; Cheng, Y.-B.; Duan, X. H. Chin. J. Chem. 2017, 35, 311. doi: 10.1002/cjoc.201600729
[24]	Kim, Y. J.; Kim, D. Y. J. Fluorine Chem. 2018, 211, 119. doi: 10.1016/j.jfluchem.2018.04.015
[25]	Kim, J. H.; Kim, D. Y. Synth. Commun. 2020, 50, 207. doi: 10.1080/00397911.2019.1692223
[26]	Wei, X.-J.; Noël, T. J. Org. Chem. 2018, 83, 11377. doi: 10.1021/acs.joc.8b01624
[27]	Zhang, F.; Liao, S.; Zhou, L.; Yang, K.; Wang, C.; Lou, Y.; Wang, C.; Song, Q. Chin. J. Chem. 2022, 40, 582. doi: 10.1002/cjoc.202100701
[28]	(a) Zheng, L.; Yang, C.; Xu, Z.; Gao, F.; Xia, W.-J. Org. Chem. 2015, 80, 5730. doi: 10.1021/acs.joc.5b00677
	(b) Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480. doi: 10.1021/ja403954g
[29]	Liu, C.; Zhang, B. RSC Adv. 2015, 5, 61199. doi: 10.1039/C5RA08996D
[30]	Tang, S.; Yuan, L.; Deng, Y.-L.; Li, Z.-Z.; Wang, L.-N.; Huang, G.-X.; Sheng, R.-L. Tetrahedron Lett. 2017, 58, 329. doi: 10.1016/j.tetlet.2016.12.027
[31]	Liu, S.; Jie, J.; Yu, J.; Yang, X. Adv. Synth. Catal. 2018, 360, 267. doi: 10.1002/adsc.201701051
[32]	Huang, H.; Li, Y. J. Org. Chem. 2017, 82, 4449. doi: 10.1021/acs.joc.7b00350
[33]	Monos, T. M.; McAtee, R. C.; Stephenson, C. R. Science 2018, 361, 1369. doi: 10.1126/science.aat2117
[34]	Yu, J.; Wu, Z.; Zhu, C. Angew. Chem., Int. Ed. 2018, 57, 17156. doi: 10.1002/anie.201811346
[35]	Whalley, D. M.; Duong, H. A.; Greaney, M. F. Chem.-Eur. J. 2019, 25, 1927. doi: 10.1002/chem.201805712 pmid: 30536854
[36]	Yu, J.; Wang, D.; Xu, Y.; Wu, Z.; Zhu, C. Adv. Synth. Catal. 2018, 360, 744. doi: 10.1002/adsc.201701229
[37]	Liu, J.; Li, W.; Xie, J.; Zhu, C. Org. Chem. Front. 2018, 5, 797. doi: 10.1039/C7QO00808B
[38]	(a) Gu, L.; Gao, Y.; Ai, X.; Jin, C.; He, Y.; Li, G.; Yuan, M. Chem. Commun. 2017, 53, 12946. doi: 10.1039/C7CC06484E
	(b) Zhang, J.-H.; Xiao, T.-F.; Ji, Z.-Q., Chen, H.-N.; Yan, P.-J.; Luo, Y.-C.; Xu, P.-F.; Xu, G.-Q. Chem. Commun. 2022, 58, 2882. doi: 10.1039/D1CC07189K
[39]	Tang, N.; Yang, S.; Wu, X.; Zhu, C. Tetrahedron 2019, 75, 1639. doi: 10.1016/j.tet.2018.12.003
[40]	Zhao, Q.; Hao, W.-J.; Shi, H.-N.; Xu, T.; Tu, S.-J.; Jiang, B. Org. Lett. 2019, 21, 9784. doi: 10.1021/acs.orglett.9b04018 pmid: 31769294
[41]	Zhang, X.-G.; Li, X.; Zhang, C.; Feng, C. Org. Lett. 2021, 23, 9611. doi: 10.1021/acs.orglett.1c03821
[42]	Ren, R.; Wu, Z.; Huan, L.; Zhu, C. Adv. Synth. Catal. 2017, 359, 3052. doi: 10.1002/adsc.201700591
[43]	Tang, X.; Studer, A. Angew. Chem., Int., Ed. 2018, 57, 814.
[44]	Nakafuku, K. M.; Fosu, S. C.; Nagib, D. A. J. Am. Chem. Soc. 2018, 140, 11202. doi: 10.1021/jacs.8b07578 pmid: 30156404
[45]	Abrams, R.; Clayden, J. Angew. Chem., nt. Ed. 2020, 59, 11600.