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

doi:10.6023/cjoc202512017

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (6): 2379-2386.DOI: 10.6023/cjoc202512017 Previous Articles Next Articles

ARTICLES

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
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: * E-mail: hailongliu@lpssy.edu.cn
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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Abstract

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

Cite this article

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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Fig. & Tab. 5

References 53

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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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