可见光引发炔烃双官能化反应构筑菲类化合物

doi:10.6023/cjoc202407009

有机化学 ›› 2025, Vol. 45 ›› Issue (2): 686-693.DOI: 10.6023/cjoc202407009 上一篇下一篇

研究论文

可见光引发炔烃双官能化反应构筑菲类化合物

李梦倩, 吕喆, 王少君, 韩宇轩, 崔秀灵^*()

华侨大学生物医学学院分子药物教育部工程研究中心福建省分子医学重点实验室福建省高校精准医学与分子诊断重点实验室厦门市海洋与基因药物重点实验室福建厦门 361021

收稿日期:2024-07-03 修回日期:2024-08-13 发布日期:2024-08-30
基金资助:
福厦泉国家自主创新协同创新项目(3502ZCQXT2021006); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(BC2018061); 华侨大学开放基金(AACCT0007)

Easy Access to Phenanthrenes Through Photoinduced Difunctionalization of Alkynes

Mengqian Li, Zhe Lv, Shaojun Wang, Yuxuan Han, Xiuling Cui()

Key Laboratory of Xiamen Marine and Gene Drugs, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Fujian Molecular Medicine, School of Biomedical Sciences, Huaqiao University, Xiamen, Fujian 361021

Received:2024-07-03 Revised:2024-08-13 Published:2024-08-30
Contact: *E-mail: cuixl@hqu.edu.cn
Supported by:
Fuxiaquan National Independent Innovation Collaborative Innovation Project(3502ZCQXT2021006); Program of Introducing Talents of Discipline to Universities (111 Project); Program of Introducing Talents of Discipline to Universities(BC2018061); Open Research Fund of Huaqiao University(AACCT0007)

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摘要/Abstract

酮酯作为双官能团化试剂, 在可见光下与二芳基炔烃反应, 以高产率获得一系列含有酰基和酯基的菲类化合物. 该策略不需要添加额外的光催化剂以及添加剂, 具有优秀的区域选择性、高效率和原子经济性.

关键词: 可见光促进, 双官能化反应, 碳-碳键活化, 菲类化合物

Ketoesters were successfully utilized as the bifunctionalization reagents to react with diaryl alkynes under visible light and photocatalyst or additives free conditions. A series of phenanthrenes containing acyl and ester groups were obtained in high yields. This protocol features with excellent regioselectivity, high efficiency, and atomic economy.

Key words: visible-light-promoted, bifunctional reaction, carbon-carbon bond activation, phenanthrenes

引用此文

李梦倩, 吕喆, 王少君, 韩宇轩, 崔秀灵. 可见光引发炔烃双官能化反应构筑菲类化合物[J]. 有机化学, 2025, 45(2): 686-693.

Mengqian Li, Zhe Lv, Shaojun Wang, Yuxuan Han, Xiuling Cui. Easy Access to Phenanthrenes Through Photoinduced Difunctionalization of Alkynes[J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 686-693.

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参考文献 32

[1]	Yao, H.; Hu, W.; Zhang, W. Molecules 2020, 26, 105.
[2]	Ren, X.; Lu, Z. Chin. J. Catal. 2019, 40, 1003.
[3]	Huang, H.; M.; Bellotti, P.; Ma, J. Nat. Rev. Chem. 2021, 5, 301. doi: 10.1038/s41570-021-00266-5 pmid: 37117839
[4]	Ma, J.; Li, J.; Meng, Q.; Zeng, X. Chin. J. Org. Chem. 2023, 43, 2040 (in Chinese).
	(马佳敏, 李姣兄, 孟千森, 曾祥华, 有机化学, 2023, 43, 2040.) doi: 10.6023/cjoc202210015
[5]	Li, M.; Zhao, D.; Sun, K. Chin. J. Org. Chem. 2022, 42, 4152 (in Chinese).
	(李猛, 赵冬阳, 孙凯, 有机化学, 2022, 42, 4152.) doi: 10.6023/cjoc202207037
[6]	Corpas, J.; Mauleón, P.; Arrayás, R. G. ACS Catal. 2021, 11, 7513.
[7]	Huang, H. M.; Bellotti, P.; Kim, S. Nat. Synth. 2022, 1, 464.
[8]	Cai, J.; Li, Y.; Ye, Z. Green Synth. Catal. 2023, 4, 253.
[9]	Xu, L.; Lu, L.; Cai, J.; Feng, Y.; Cui, X. Chin. J. Org. Chem. 2022, 42, 1210 (in Chinese).
	(许丽梅, 卢林燕, 蔡尽忠, 冯亚栋, 崔秀灵, 有机化学, 2022, 42, 1210.) doi: 10.6023/cjoc202110022
[10]	Long, L.; Wang, J.; Gu, L. J. Org. Chem. 2021, 86, 12084.
[11]	Ma, C.; Tian, Y.; Wang, J. Org. Lett. 2022, 24, 8265.
[12]	Matsumoto, A.; Lee, H.-J.; Maruoka, K. Chem. Rec. 2021, 21, 1342.
[13]	Murugesan, V.; Muralidharan, A.; Anantharaj, G. V. Org. Lett. 2022, 24, 8435.
[14]	Rao, W. H.; Li, Q.; Jiang, L. L. J. Org. Chem. 2022, 87, 14194.
[15]	Jung, S.; Kim, J.; Hong, S. Adv. Synth. Catal. 2017, 359, 3882.
[16]	Luo, Y.; Wei, Q.; Yang, L. ACS. Catal. 2022, 12, 12984.
[17]	Wang, H.; Li, T.; Hu, D. Org. Lett. 2021, 23, 3772.
[18]	Wang, Z.; Liu, Q.; Ji, X. ACS. Catal. 2020, 10, 154.
[19]	Sui, J. L.; Zhong, L.-J.; Xiong, B.-Q. Chem. Commun. 2024, 60, 4834.
[20]	Tang, K.; Su, F.; Pan, S. Chin. Chem. Lett. 2024, 35, 109495.
[21]	Tan, H.; Li, H.; Ji, W. Angew. Chem., Int. Ed. 2015, 54, 8374.
[22]	Slutskyy, Y.; Overman, L. E. Org. Lett. 2016, 18, 2564. doi: 10.1021/acs.orglett.6b00895 pmid: 27186995
[23]	Weires, N. A.; Slutskyy, Y.; Overman, L. E. Angew. Chem.,Int. Ed. 2019, 58, 8561.
[24]	Xu, X.; Tang, Y.; Li, X. J. Org. Chem. 2014, 79, 446.
[25]	Chen, J. Q.; Tu, X., Qin, B. Org. Lett. 2022, 24, 642.
[26]	Xiao, H. X.; Li, P.-P.; Pan, B. J. Org. Chem. 2023, 88, 5861.
[27]	Chen, J.Q.; Chen, Q.; Chen, B. Org. Chem. Front. 2023, 10, 2018.
[28]	Zheng, J.; Dong, X.; Yoon, T. P. Org. Lett. 2020, 22, 6520. doi: 10.1021/acs.orglett.0c02314 pmid: 32806138
[29]	Rykaczewski, K. A.; Schindler, C. S. Org. Lett. 2020, 22, 6516. doi: 10.1021/acs.orglett.0c02316 pmid: 32806149
[30]	Liang, Y.; Kleinmans, R.; Daniliuc, C. G. J. Am. Chem. Soc. 2022, 144, 20207.
[31]	He, X.; Gao, Y.; Nie, J. Macromolecules 2021, 54, 3854.
[32]	Kang, U.; Cartner, L. K.; Wang, D. J. Nat. Prod. 2020, 83, 3464.

Entry	1a/equiv.	Solvent	Light source	Yield^b/%
1	1	CF₃CH₂OH	400~405 nm	38
2	2	CF₃CH₂OH	400~405 nm	75
3	3	CF₃CH₂OH	400~405 nm	81
4	3	CH₂Cl₂	400~405 nm	Trace
5	3	1,1,2-Trichloroethane	400~405 nm	Trace
6	3	Toluene	400~405 nm	Trace
7	3	1,4-Dioxane	400~405 nm	Trace
8	3	DMSO	400~405 nm	Trace
9	3	DMF	400~405 nm	Trace
10	3	THF	400~405 nm	Trace
11	3	CH₃CN	400~405 nm	Trace
12	3	CH₃OH	400~405 nm	30
13	3	CF₃CH₂OH	405~410 nm	75
14	3	CF₃CH₂OH	395~400 nm	90
15^c	3	CF₃CH₂OH	395~400 nm	Trace
16	3	CF₃CH₂OH	390~395 nm	89
17^d	3	CF₃CH₂OH	395~400 nm	90
18^e	3	CF₃CH₂OH	—	N.R.

Entry	1a/equiv.	Solvent	Light source	Yield^b/%
1	1	CF₃CH₂OH	400~405 nm	38
2	2	CF₃CH₂OH	400~405 nm	75
3	3	CF₃CH₂OH	400~405 nm	81
4	3	CH₂Cl₂	400~405 nm	Trace
5	3	1,1,2-Trichloroethane	400~405 nm	Trace
6	3	Toluene	400~405 nm	Trace
7	3	1,4-Dioxane	400~405 nm	Trace
8	3	DMSO	400~405 nm	Trace
9	3	DMF	400~405 nm	Trace
10	3	THF	400~405 nm	Trace
11	3	CH₃CN	400~405 nm	Trace
12	3	CH₃OH	400~405 nm	30
13	3	CF₃CH₂OH	405~410 nm	75
14	3	CF₃CH₂OH	395~400 nm	90
15^c	3	CF₃CH₂OH	395~400 nm	Trace
16	3	CF₃CH₂OH	390~395 nm	89
17^d	3	CF₃CH₂OH	395~400 nm	90
18^e	3	CF₃CH₂OH	—	N.R.

可见光引发炔烃双官能化反应构筑菲类化合物

Easy Access to Phenanthrenes Through Photoinduced Difunctionalization of Alkynes

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