无光催化剂条件下可见光诱导炔基碘和亚磺酸钠偶联反应

doi:10.6023/cjoc202306023

摘要/Abstract

报道了一种由可见光促进的炔碘与亚磺酸钠直接交叉偶联构建炔砜的方法. 合成方法简便、绿色, 不需要任何光催化剂和添加剂, 具有良好的官能团耐受性和底物普遍适应性. 此外, 放大规模实验也能取得良好的收率, 进一步证明了该方法的实际应用价值.

The cross-coupling reaction between alkynyl iodide and sodium sulphinate catalyzed by visible light, leading to the construction of acetylene sulfone, is reported. The synthesis method is simple and green, and does not require any photo- catalyst and additive. The reaction has high efficiency and good functional group compatibility. In addition, the scale-up experiment can also obtain good yield, which further proves the practical application value of the reaction.

Key words: alkyne sulfone, visible light, alkynyl iodine, sodium sulphinate, coupling reaction

引用此文

陈雯雯, 张琴, 张松月, 黄芳芳, 张馨尹, 贾建峰. 无光催化剂条件下可见光诱导炔基碘和亚磺酸钠偶联反应[J]. 有机化学, 2024, 44(2): 584-592.

Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.

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Entry	Light source	Atmosphere	I₂	Cat.	Yield^b/%
1^c^,^d	White LED	O₂	I₂	BiOCl	54
2^c	White LED	O₂	I₂	—	42
3^d	White LED	O₂	—	BiOCl	62
4	White LED	O₂	—	—	60
5	Blue LED	O₂	—	—	39
6	Red LED	O₂	—	—	29
7	Green LED	O₂	—	—	35
8	White LED	Air	—	—	60
9	White LED	N₂	—	—	44
10^e	—	Air	—	—	27
11^f	—	Air	—	—	16

Entry	Light source	Atmosphere	I₂	Cat.	Yield^b/%
1^c^,^d	White LED	O₂	I₂	BiOCl	54
2^c	White LED	O₂	I₂	—	42
3^d	White LED	O₂	—	BiOCl	62
4	White LED	O₂	—	—	60
5	Blue LED	O₂	—	—	39
6	Red LED	O₂	—	—	29
7	Green LED	O₂	—	—	35
8	White LED	Air	—	—	60
9	White LED	N₂	—	—	44
10^e	—	Air	—	—	27
11^f	—	Air	—	—	16

Entry	Solvent	Additive	Yield^b/%
1	1,4-Dioxane	—	68
2	CH₃CN	—	76
3	MeOH	—	26
4	DCE	—	67
5	DMF	—	31
6	Toluene	—	43
7	DMSO	—	19
8	H₂O	—	38
9	TFE	—	61
10	C₇H₅F₃	—	45
11^c	CH₃CN/H₂O	—	57
12^d	CH₃CN/H₂O	—	62
13	CH₃CN	K₂CO₃(1.0 equiv.)	58
14	CH₃CN	NEt₃(1.0 equiv.)	33
15	CH₃CN	HCl (1.0 equiv.)	63
16	CH₃CN	CH₃COOH (1.0 equiv.)	54
17	CH₃CN	TBAI (0.2 equiv.)	33

Entry	Solvent	Additive	Yield^b/%
1	1,4-Dioxane	—	68
2	CH₃CN	—	76
3	MeOH	—	26
4	DCE	—	67
5	DMF	—	31
6	Toluene	—	43
7	DMSO	—	19
8	H₂O	—	38
9	TFE	—	61
10	C₇H₅F₃	—	45
11^c	CH₃CN/H₂O	—	57
12^d	CH₃CN/H₂O	—	62
13	CH₃CN	K₂CO₃(1.0 equiv.)	58
14	CH₃CN	NEt₃(1.0 equiv.)	33
15	CH₃CN	HCl (1.0 equiv.)	63
16	CH₃CN	CH₃COOH (1.0 equiv.)	54
17	CH₃CN	TBAI (0.2 equiv.)	33