铜催化的Sonogashira偶联/亲电环化构建3-(苯硒基)苯并呋喃衍生物

doi:10.6023/cjoc202512017

有机化学 ›› 2026, Vol. 46 ›› Issue (6): 2379-2386.DOI: 10.6023/cjoc202512017 上一篇下一篇

研究论文

铜催化的Sonogashira偶联/亲电环化构建3-(苯硒基)苯并呋喃衍生物

刘妍伶^a, 张毅涵^b, 陈霞^b, 周晓玉^b, 崔颖娜^a, 刘海龙^b^,^*()

^a 大连大学环境与化学工程学院辽宁大连 116622
^b 六盘水师范学院化学与材料工程学院贵州 553004

收稿日期:2026-02-02 修回日期:2026-03-03 发布日期:2026-04-20
通讯作者: 刘海龙
基金资助:
贵州省教育厅青年科技人才成长(黔教技[2025]35号); 贵州省自然科学基金(黔科合基础-ZK[2023]重点048号); 贵州省教育厅基金(黔教技[2023]088号); 高层次人才科研启动基金(No. LPSSY-KYJJ201909); 六盘水师范学院科研培育(LPSSYLPY202411); 贵州省大学生创新创业训练(S2024109771720); 贵州省煤炭清洁利用重点实验室(黔科合平台-人才[2020]2001号); 六盘水师范学院科技创新团队(LPSSYKJTD201904)

Copper-Catalyzed Sonogashira Coupling/Electrophilic Cyclization to Construct 3-(Phenylselanyl)benzofuran Derivatives

Yanling Liu^a, Yihan Zhang^b, Xia Chen^b, Xiaoyu Zhou^b, Yingna Cui^a, Hailong Liu^b^,^*()

^a College of Environmental and Chemical Engineering, Dalian University, Dalian, Liaoning 116622
^b Liupanshui Normal University, School of Chemistry and Materials Engineering, Guizhou 553004

Received:2026-02-02 Revised:2026-03-03 Published:2026-04-20
Contact: Hailong Liu
Supported by:
Project supported by the Youth Science and Technology Talent Growth Program of the Guizhou Provincial Department of Education (Qian Jiao Ji [2025] No. 35); Natural Science Foundation of Guizhou Province (Qian Ke He Basic-ZK [2023] Key Project No. 048); Foundation of Guizhou Educational Committee (Qian Jiao Ji [2023] No. 088); High-level Talent Scientific Research Startup Fund (No. LPSSY-KYJJ201909); Scientific Research Cultivation Project of Liupanshui Normal University(LPSSYLPY202411); Guizhou Provincial Undergraduate Innovation and Entrepreneurship Training Program(S2024109771720); Guizhou Key Laboratory of Clean Coal Utilization (Qian Ke He Platform-Talent [2020] No. 2001); Scientific and Technological Innovation Team of Liupanshui Normal University(LPSSYKJTD201904)

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摘要/Abstract

发展了一种基于铜催化体系的Sonogashira交叉偶联/亲电环化串联反应策略, 通过连续反应高效构建苯并呋喃骨架. 该催化体系无需惰性气体保护及中间体分离纯化, 操作简便且条件温和. 实验结果表明, 该反应对底物具有优异的普适性, 无论是富电子或缺电子取代的邻碘苯甲醚, 还是结构多样的苯乙炔衍生物, 均能以良好至优异的收率获得目标产物. 此外, 该方法的步骤高效性为芳炔类化合物的合成提供了一种实用且绿色的新途径.

关键词: Sonogashira交叉偶联, 铜催化, 串联反应, 苯并呋喃衍生物

A Sonogashira cross-coupling/electrophilic cyclization tandem reaction strategy based on a copper-catalyzed system is developed, efficiently constructing benzofuran frameworks through consecutive reactions. This catalytic system does not require inert gas protection or intermediate separation and purification, making it simple to operate under mild conditions. Experimental results show that the reaction exhibits excellent substrate tolerance. Whether it is an electron-rich or electron- deficient ortho-iodophenyl ether, or structurally diverse phenylacetylene derivatives, the target products can be obtained in good to excellent yields. Moreover, the efficiency of this method provides a practical and green new approach for the synthesis of arylacetylene compounds.

Key words: Sonogashira cross-coupling, copper catalysis, tandem reaction, benzofuran derivative

引用此文

刘妍伶, 张毅涵, 陈霞, 周晓玉, 崔颖娜, 刘海龙. 铜催化的Sonogashira偶联/亲电环化构建3-(苯硒基)苯并呋喃衍生物[J]. 有机化学, 2026, 46(6): 2379-2386.

Yanling Liu, Yihan Zhang, Xia Chen, Xiaoyu Zhou, Yingna Cui, Hailong Liu. Copper-Catalyzed Sonogashira Coupling/Electrophilic Cyclization to Construct 3-(Phenylselanyl)benzofuran Derivatives[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2379-2386.

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参考文献 53

[1]	Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
[2]	Docherty, J. H.; Lister, T. M.; McArthur, G.; Findlay, M. T.; Domingo-Legarda, P.; Kenyon, J.; Choudhary, S.; Larrosa, I. Chem. Rev. 2023, 123, 7692.
[3]	Zhao, X.; Liu, W. Synthesis 2024, 56, 1244.
[4]	(a) Dong, W.-F.; Wang, N.; Yang, H.; Xu, G.-Q.; Tang, W.-J. Acta Chim. Sinica 2024, 82, 940. (in Chinese)
	(董文锋, 王楠, 杨贺, 徐广庆, 汤文军, 化学学报, 2024, 82, 940.)
	(b) Dong, W.-F.; Wang, N.; Yang, H.; Xu, G.-Q.; Tang, W.-J. Acta Chim. Sinica 2024, 82, 1044. (in Chinese)
	(董文锋, 王楠, 杨贺, 徐广庆, 汤文军, 化学学报, 2024, 82, 1044.)
[5]	Yang, X.; Liu, Y.-L.; Chen, X.; Zhou, X.-Y.; Wang, A.-L.; Liu, H.-L. Acta Chim. Sinica 2025, 83, 354. (in Chinese)
	(杨雪, 刘妍伶, 陈霞, 周晓玉, 王爱玲, 刘海龙, 化学学报, 2025, 83, 354.)
[6]	Wan, B.; Chen, Y.-T.; Wen, M.-H.; Mai, S.-Y.; Qiu, F.; Du, Q.-F. Acta Chim. Sinica 2025, 83, 1129. (in Chinese)
	(万贝, 陈玉婷, 文睦豪, 麦少瑜, 邱峰, 杜庆锋, 化学学报, 2025, 83, 1129.)
[7]	Zhang, D.-W.; Zhao, H.-Y.; Feng, X.-T.; Gu, Y.-C.; Zhang, X.-G. Acta Chim. Sinica 2024, 82, 105. (in Chinese)
	(张大伟, 赵海洋, 冯笑甜, 顾玉诚, 张新刚, 化学学报, 2024, 82, 105.)
[8]	Wen, Y.-C.; Zhu, L.-J.; Yi, R.-N.; Shen, C.; Zhu, H.-T.; Wang, Z.-L.; He, W.-M. Acta Chim. Sinica 2025, 83, 1124. (in Chinese)
	(文延萃, 朱丽君, 易荣楠, 沈超, 祝海涛, 王祖利, 何卫民, 化学学报, 2025, 83, 1124.)
[9]	Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874.
[10]	Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
[11]	Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084.
[12]	Manoni, F.; Rumo, C.; Li, L.; Harran, P. G. J. Am. Chem. Soc. 2018, 140, 1280.
[13]	Casotti, G.; Fusini, G.; Ferreri, M.; Pardini, L. F.; Evangelisti, C.; Angelici, G.; Carpita, A. Synthesis 2020, 52, 1795.
[14]	Lumbreras-Teijeiro, A.; Bacic, M.; Oliver-Meseguer, J.; Leyva-Pérez, A. Chem.-Eur. J. 2022, 28, e202202421.
[15]	Darbem, P. M.; Esteves, H. A.; Burrow, R. A.; Soares-Paulino, A. A.; Pimenta, D. C.; Stefani, H. A. RSC Adv. 2022, 12, 2145.
[16]	Nishimura, K.; Kinugawa, M. Org. Process Res. Dev. 2012, 16, 225.
[17]	Collet, J. W.; Ackermans, K.; Lambregts, J.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. J. Org. Chem. 2018, 83, 854.
[18]	Tamardash, L. K.; Bakherad, M.; Keivanloo, A.; Notash, B. ChemElectroChem 2023, 8, e202204985.
[19]	Huang, Z.; Xie, N.; Illes, P.; Di Virgilio, F.; Ulrich, H.; Semyanov, A.; Verkhratsky, A.; Sperlagh, B.; Yu, S. G.; Huang, C.; Tang, Y. Signal Transduction Targeted Ther. 2021, 6, 162.
[20]	Tang, Z.; Xu, S.; Yin, N.; Yang, Y.; Deng, Q.; Shen, J.; Zhang, X.; Wang, T.; He, H.; Lin, X.; Zhou, Y.; Zou, Z. Adv. Mater. 2023, 35, 2210693.
[21]	Zang, Y.; Gao, S.; Jing, B.; Sun, H.; Wang, J.; Liu, J.; Miao, F.; Xu, L. J. Mater. Sci. 2023, 58, 170.
[22]	Choy, P. Y.; Gan, K. B.; Kwong, F. Y. Chin. J. Chem. 2023, 41, 1099.
[23]	Kanwal, I.; Mujahid, A.; Rasool, N.; Rizwan, K.; Malik, A.; Ahmad, G.; Shah, S. A. A.; Rashid, U.; Nasir, N. M. Catalysts 2020, 10, 443.
[24]	Yang, Q.; Babij, N. R.; Good, S. Org. Process Res. Dev. 2019, 23, 2608.
[25]	Miao, Y. H.; Hu, Y. H.; Yang, J.; Liu, T.; Sun, J.; Wang, X. J. RSC Adv. 2019, 9, 27510.
[26]	Farhat, J.; Alzyoud, L.; Alwahsh, M.; Al-Omari, B. Cancers 2022, 14, 2196.
[27]	Zhang, L.; Xiao, J.; Wang, Y.-W.; Peng, Y. Acta Chim. Sinica 2022, 80, 1152. (in Chinese)
	(张崃, 肖检, 王雅雯, 彭羽, 化学学报, 2022, 80, 1152.)
[28]	Irfan, A.; Zahoor, A. F.; Rasul, A.; Al-Hussain, S. A.; Faisal, S.; Ahmad, S.; Noor, R.; Muhammed, M. T.; Zaki, M. E. A. Int. J. Mol. Sci. 2023, 24, 3008.
[29]	Irfan, A.; Faiz, S.; Rasul, A.; Zafar, R.; Zahoor, A. F.; Kotwica- Mojzych, K.; Mojzych, M. Molecules 2022, 27, 1023.
[30]	Irfan, A.; Faisal, S.; Ahmad, S.; Saif, M. J.; Zahoor, A. F.; Khan, S. G.; Javid, J.; Al-Hussain, S. A.; Muhammed, M. T.; Zaki, M. E. A. Biomedicines 2023, 11, 3085.
[31]	Faiz, S.; Zahoor, A. F.; Ajmal, M.; Kamal, S.; Ahmad, S.; Abdelgawad, A. M.; Elnaggar, M. E. J. Heterocycl. Chem. 2019, 56, 2839.
[32]	Saeed, S.; Zahoor, A. F.; Kamal, S.; Raza, Z.; Bhat, M. A. Molecules 2023, 28, 6007.
[33]	Irfan, A.; Faisal, S.; Zahoor, A. F.; Noreen, R.; Al-Hussain, S. A.; Tuzun, B.; Javaid, R.; Elhenawy, A. A.; Zaki, M. E. A.; Ahmad, S.; Abdellattif, M. H. Pharmaceuticals 2023, 16, 829.
[34]	Xu, Z.; Xu, D.; Zhou, W.; Zhang, X. Curr. Top. Med. Chem. 2022, 22, 64.
[35]	Pagotti, M. C.; Dias, H. J.; Candido, A. C. B. B.; Oliveira, T. A. S.; Borges, A.; Oliveira, N. D.; Lopes, C. D.; Orenha, R. P.; Parreira, R. L. T.; Crotti, A. E. M.; Magalhães, L. G. Pharmaceutics 2023, 15, 754.
[36]	Wang, B.; Zhang, Q.; Luo, J.; Gan, Z.; Jiang, W.; Tang, Q. Molecules 2019, 24, 2187.
[37]	Laurita, T.; D’Orsi, R.; Chiummiento, L.; Funicello, M.; Lupattelli, P. Synthesis 2020, 52, 1451.
[38]	Tan, J.; Wang, R.; Xu, L.; Wu, W.; Deng, M.; Yuan, W.; Li, L.; Lin, Z. Adv. Synth. Catal. 2023, 365, 983.
[39]	Coaviche-Yoval, A.; Luna, H.; Tovar-Miranda, R.; Soriano-Ursúa, M. A.; Trujillo-Ferrara, J. G. Med. Chem. 2019, 15, 77.
[40]	Singh, A.; Singh, S.; Ghosh, K.; Ahmed, N. Synthesis 2023, 55, 4191.
[41]	Yang, X.; Sun, R. Adv. Synth. Catal. 2023, 365, 124.
[42]	Jin, R.-W.; Wang, L.-J.; Song, Y.; Liu, X.-P.; Wang, J.-W.; Li, Z.-X. Chin. J. Org. Chem. 2024, 44, 2742. (in Chinese)
	(靳瑞文, 王连杰, 宋跃, 刘小培, 王俊伟, 李中贤, 有机化学, 2024, 44, 2742.)
[43]	Huang, W.; Xu, J.; Liu, C.; Chen, Z.; Gu, Y. J. Org. Chem. 2019, 84, 2941.
[44]	Roy, A.; Biswas, S.; Duari, S.; Maity, S.; Mishra, A. K.; de Souza, A. R.; Elsharif, A. M.; Morgon, N. H.; Biswas, S. J. Org. Chem. 2023, 88, 15580.
[45]	Zhang, J.; Zhang, X.; Wang, T.; Yao, X.; Wang, P.; Wang, P.; Jing, S.; Liang, Y.; Zhang, Z. J. Org. Chem. 2017, 82, 12097.
[46]	He, H.; Lü L.-L.; Liu, J.-Q.; Wang, X.-S. Chin. J. Org. Chem. 2024, 44, 3427. (in Chinese)
	(何姮, 吕兰兰, 刘建全, 王香善, 有机化学, 2024, 44, 3427.)
[47]	Vadakkethil Arundhathi, K.; Vaishnavi, P.; Aneeja, T.; Anilkumar, G. RSC Adv. 2023, 13, 4823.
[48]	Chen, X.; Zhou, X.-Y. Synthesis 2023, 55, 1213.
[49]	Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
[50]	Xavier, M. C. D. F.; Sandagorda, E. M. A.; Neto, J. S. S.; Schumacher, R. F.; Silva, M. S. RSC Adv. 2020, 10, 13975.
[51]	An, C.; Li, C.-Y.; Huang, X.-B.; Gao, W.-X.; Zhou, Y.-B.; Liu, M.-C.; Wu, H.-Y. Org. Lett. 2019, 21, 6710.
[52]	Blödorn, G. B.; Duarte, L. F. B.; Roehrs, J. A.; Silva, M. S.; Neto, J. S. S.; Alves, D. Eur. J. Org. Chem. 2022, 2022, e202200775.
[53]	Hasimujiang, B.; Lin, S.; Zheng, C.; Zeng, Y.; Ruan, Z. Molecules 2022, 27, 6314.

Entry	Deviation from standard conditions	Yield^b/%
1	CuCl instead of CuBH₄(PPh₃)₂	Trace
2	CuBr instead of CuBH₄(PPh₃)₂	Trace
3	Cu₂O instead of CuBH₄(PPh₃)₂	Trace
4	CuC₂O₄ instead of CuBH₄(PPh₃)₂	Trace
5	CuO instead of CuBH₄(PPh₃)₂	Trace
6	Cu(OAc)₂ instead of CuBH₄(PPh₃)₂	Trace
7	Cu(OTf)₂ instead of CuBH₄(PPh₃)₂	Trace
8	CuI instead of CuBH₄(PPh₃)₂	Trace
9	CuBH₄(PPh₃)₂	>99 (>99)^c
10	1.0 mol% CuBH₄(PPh₃)₂ instead of 5 mol% CuBH₄(PPh₃)₂	85
11	3.0 mol% CuBH₄(PPh₃)₂ instead of 5 mol% CuBH₄(PPh₃)₂	90
12	KOAc instead of DBU	Trace
13	NEt₃ instead of DBU	Trace
14	KOH instead of DBU	Trace
15	Cs₂CO₃ instead of DBU	98
16	K₂CO₃ instead of DBU	97
17	CsF instead of DBU	99
18	Cs₂WO₄ instead of DBU	46
19	DBU	99
20	1.0 equiv. DBU instead of 1.5 equiv. DBU	85
21	EtOH	99
22	DMSO	81
23	1,4-Dioxane	65
24	DCM	Trace
25	CH₃CN	99
26	DMC	20
27	DEC	30
28	80 ℃ instead of 130 ℃	24
29	100 ℃ instead of 130 ℃	32
30	120 ℃ instead of 130 ℃	89
31	125 ℃ instead of 130 ℃	92
32	12 h instead of 24 h	87

Entry	Deviation from standard conditions	Yield^b/%
1	CuCl instead of CuBH₄(PPh₃)₂	Trace
2	CuBr instead of CuBH₄(PPh₃)₂	Trace
3	Cu₂O instead of CuBH₄(PPh₃)₂	Trace
4	CuC₂O₄ instead of CuBH₄(PPh₃)₂	Trace
5	CuO instead of CuBH₄(PPh₃)₂	Trace
6	Cu(OAc)₂ instead of CuBH₄(PPh₃)₂	Trace
7	Cu(OTf)₂ instead of CuBH₄(PPh₃)₂	Trace
8	CuI instead of CuBH₄(PPh₃)₂	Trace
9	CuBH₄(PPh₃)₂	>99 (>99)^c
10	1.0 mol% CuBH₄(PPh₃)₂ instead of 5 mol% CuBH₄(PPh₃)₂	85
11	3.0 mol% CuBH₄(PPh₃)₂ instead of 5 mol% CuBH₄(PPh₃)₂	90
12	KOAc instead of DBU	Trace
13	NEt₃ instead of DBU	Trace
14	KOH instead of DBU	Trace
15	Cs₂CO₃ instead of DBU	98
16	K₂CO₃ instead of DBU	97
17	CsF instead of DBU	99
18	Cs₂WO₄ instead of DBU	46
19	DBU	99
20	1.0 equiv. DBU instead of 1.5 equiv. DBU	85
21	EtOH	99
22	DMSO	81
23	1,4-Dioxane	65
24	DCM	Trace
25	CH₃CN	99
26	DMC	20
27	DEC	30
28	80 ℃ instead of 130 ℃	24
29	100 ℃ instead of 130 ℃	32
30	120 ℃ instead of 130 ℃	89
31	125 ℃ instead of 130 ℃	92
32	12 h instead of 24 h	87

Entry^a	Electrophile	Solvent	Yield^b/%
1	I₂	CH₂Cl₂	Trace
2	ICl	CH₂Cl₂	Trace
3	BCl₃	CH₂Cl₂	Trace
4	PhSeCl	CH₂Cl₂	>99
5	PhSeCl	DMSO	30
6	PhSeCl	MeCN	49
7	PhSeCl	THF	66
8	PhSeCl	CH₂Cl₂	34^c
9	PhSeCl	CH₂Cl₂	67^d

Entry^a	Electrophile	Solvent	Yield^b/%
1	I₂	CH₂Cl₂	Trace
2	ICl	CH₂Cl₂	Trace
3	BCl₃	CH₂Cl₂	Trace
4	PhSeCl	CH₂Cl₂	>99
5	PhSeCl	DMSO	30
6	PhSeCl	MeCN	49
7	PhSeCl	THF	66
8	PhSeCl	CH₂Cl₂	34^c
9	PhSeCl	CH₂Cl₂	67^d

铜催化的Sonogashira偶联/亲电环化构建3-(苯硒基)苯并呋喃衍生物

Copper-Catalyzed Sonogashira Coupling/Electrophilic Cyclization to Construct 3-(Phenylselanyl)benzofuran Derivatives

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