Visible Light-Induced Synthesis of Polysubstituted Dihydrofurans via Cyclization of Aromatic Aldehydes with Acrylonitriles

doi:10.6023/cjoc202406003

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (5): 1763-1769.DOI: 10.6023/cjoc202406003 Previous Articles Next Articles

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可见光诱导芳香醛与苄烯丙二腈环化合成多取代二氢呋喃

田曈^a, 陈镤^a, 黄华文^a^,^b^,^*()

^a 湘潭大学化学学院湖南湘潭 411105
^b 河南师范大学化学化工学院河南新乡 453007

收稿日期:2024-06-03 修回日期:2024-07-03 发布日期:2024-07-25
基金资助:
国家自然科学基金(22071211); 河南师范大学化学化工学院开放基金(2022C02)

Visible Light-Induced Synthesis of Polysubstituted Dihydrofurans via Cyclization of Aromatic Aldehydes with Acrylonitriles

Tong Tian^a, Pu Chen^a, Huawen Huang^a^,^b^,^*()

^a College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105
^b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2024-06-03 Revised:2024-07-03 Published:2024-07-25
Contact: * E-mail: hwhuang@xtu.edu.cn
Supported by:
National Natural Science Foundation of China(22071211); Open Research Fund of School of Chemistry and Chemical Engineering of Henan Normal University(2022C02)

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Abstract

A synthetic method for multi-substituted 4,5-dihydrofuran compounds through tandem Giese addition/cyclization process under visible light-induced photoredox catalysis from aromatic aldehydes and 2-benzylidenemalononitriles is reported. The reaction was carried out in the absence of transition metal catalysts, providing a simple and stereoselective approach for constructing multi-substituted 4,5-dihydrofurans and making it an important supplement to existing methods.

Key words: dihydrofuran, visible light irradiation, Giese reaction, cyclization, aldehyde

Cite this article

Tong Tian, Pu Chen, Huawen Huang. Visible Light-Induced Synthesis of Polysubstituted Dihydrofurans via Cyclization of Aromatic Aldehydes with Acrylonitriles[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1763-1769.

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Fig. & Tab. 8

References 16

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Entry	Photocatalyst	Solvent	RE	Additive	Yield^b/%
1	4CzIPN	Toluene	HE	NaBr	58
2	4CzTPN	Toluene	HE	NaBr	54
3	fac-Ir(ppy)₃	Toluene	HE	NaBr	50
4	[Ir]PF₆	Toluene	HE	NaBr	Trace
5	Ru(bpy)₃Cl₂	Toluene	HE	NaBr	n.d.
6	Eosin Y	Toluene	HE	NaBr	n.d.
7	4CzIPN	Toluene	DABCO	NaBr	n.d.
8	4CzIPN	Toluene	DBU	NaBr	n.d.
9	4CzIPN	Toluene	Et₃N	NaBr	n.d.
10	4CzIPN	Toluene	PhSiH₃	NaBr	n.d.
11	4CzIPN	Toluene	Et₃SiH	NaBr	n.d.
12	4CzIPN	DCM	HE	NaBr	55
13	4CzIPN	DCE	HE	NaBr	52
14	4CzIPN	Acetone	HE	NaBr	29
15	4CzIPN	Mesitylene	HE	NaBr	38
16	4CzIPN	PhCl	HE	NaBr	50
17	4CzIPN	Toluene	HE	Ni(acac)₂	33
18	4CzIPN	Toluene	HE	NiCl₂•6H₂O	60
19	4CzIPN	Toluene	HE	CuSO₄	69
20	4CzIPN	Toluene	HE	FeSO₄•7H₂O	68
21	4CzIPN	Toluene	HE	Fe₂(SO₄)₃	63
22	4CzIPN	Toluene	HE	Na₂SO₄	71
23	—	Toluene	HE	Na₂SO₄	n.d.
24	4CzIPN	Toluene	—	Na₂SO₄	n.d.
25	4CzIPN	Toluene	HE	—	50
26^c	4CzIPN	Toluene	HE	Na₂SO₄	63
27^d	4CzIPN	Toluene	HE	Na₂SO₄	70

Entry	Photocatalyst	Solvent	RE	Additive	Yield^b/%
1	4CzIPN	Toluene	HE	NaBr	58
2	4CzTPN	Toluene	HE	NaBr	54
3	fac-Ir(ppy)₃	Toluene	HE	NaBr	50
4	[Ir]PF₆	Toluene	HE	NaBr	Trace
5	Ru(bpy)₃Cl₂	Toluene	HE	NaBr	n.d.
6	Eosin Y	Toluene	HE	NaBr	n.d.
7	4CzIPN	Toluene	DABCO	NaBr	n.d.
8	4CzIPN	Toluene	DBU	NaBr	n.d.
9	4CzIPN	Toluene	Et₃N	NaBr	n.d.
10	4CzIPN	Toluene	PhSiH₃	NaBr	n.d.
11	4CzIPN	Toluene	Et₃SiH	NaBr	n.d.
12	4CzIPN	DCM	HE	NaBr	55
13	4CzIPN	DCE	HE	NaBr	52
14	4CzIPN	Acetone	HE	NaBr	29
15	4CzIPN	Mesitylene	HE	NaBr	38
16	4CzIPN	PhCl	HE	NaBr	50
17	4CzIPN	Toluene	HE	Ni(acac)₂	33
18	4CzIPN	Toluene	HE	NiCl₂•6H₂O	60
19	4CzIPN	Toluene	HE	CuSO₄	69
20	4CzIPN	Toluene	HE	FeSO₄•7H₂O	68
21	4CzIPN	Toluene	HE	Fe₂(SO₄)₃	63
22	4CzIPN	Toluene	HE	Na₂SO₄	71
23	—	Toluene	HE	Na₂SO₄	n.d.
24	4CzIPN	Toluene	—	Na₂SO₄	n.d.
25	4CzIPN	Toluene	HE	—	50
26^c	4CzIPN	Toluene	HE	Na₂SO₄	63
27^d	4CzIPN	Toluene	HE	Na₂SO₄	70

可见光诱导芳香醛与苄烯丙二腈环化合成多取代二氢呋喃

Visible Light-Induced Synthesis of Polysubstituted Dihydrofurans via Cyclization of Aromatic Aldehydes with Acrylonitriles

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