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

doi:10.6023/cjoc202406003

摘要/Abstract

由芳香醛和苄烯丙二腈出发, 发展了基于可见光诱导串联Giese加成-环化反应过程的4,5-二氢呋喃衍生物的合成新方法. 该反应无需过渡金属催化剂, 为构建多取代二氢呋喃衍生物提供了简便且立体选择性的制备路径, 是现有方法的重要补充.

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

引用此文

田曈, 陈镤, 黄华文. 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[J]. 有机化学, 2025, 45(5): 1763-1769.

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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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