CuI/4-Hydroxy Picolinohydrazide Catalyzed Coupling Reaction of (Hetero)aryl Chlorides with Sodium Aryl Sulfinates

doi:10.6023/cjoc202411014

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (4): 1276-1282.DOI: 10.6023/cjoc202411014 Previous Articles Next Articles

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碘化亚铜/4-羟基吡啶酰肼催化的(杂)芳基氯代物和苯基亚磺酸钠的偶联反应

李赛洛^a, 马大为^b^,^*()

a 上海科技大学物质学院上海 201210
b 中国科学院上海有机化学研究所生命过程小分子调控全国重点实验室上海 200032

收稿日期:2024-11-14 修回日期:2024-11-26 发布日期:2024-11-28
基金资助:
国家自然科学基金(21991110)

CuI/4-Hydroxy Picolinohydrazide Catalyzed Coupling Reaction of (Hetero)aryl Chlorides with Sodium Aryl Sulfinates

Sailuo Li^a, Dawei Ma^b()

a School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210
b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2024-11-14 Revised:2024-11-26 Published:2024-11-28
Contact: * E-mail: madw@sioc.ac.cn
Supported by:
National Natural Science Foundation of China(21991110)

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Abstract

By using a newly developed 4-hydroxy picolinohydrazide as the ligand, Cu-catalyzed coupling of (hetero)aryl chlorides with sodium aryl sulfonates proceeded smoothly at 130 ℃ to give a series of biarylsulfones in 53%~96% yields. This represents the first metal-catalyzed coupling reaction of (hetero)aryl chlorides with sodium aryl sulfonates. Aryl and heteroaryl chlorides bearing either electron-donating or electron-withdrawing groups were applicable for this coupling reaction.

Key words: coupling reaction, copper catalysis, ligand, (hetero)aryl chloride, biarylsulfone

Cite this article

Sailuo Li, Dawei Ma. CuI/4-Hydroxy Picolinohydrazide Catalyzed Coupling Reaction of (Hetero)aryl Chlorides with Sodium Aryl Sulfinates[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1276-1282.

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Fig. & Tab. 4

References 10

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Entry	Copper salt	Ligand	Base	Solvent	Temp./℃	Yield^b/%
1	CuI	L1	K₃PO₄	DMSO	120	11
2	CuI	L2	K₃PO₄	DMSO	120	12
3	CuI	L3	K₃PO₄	DMSO	120	33
4	CuI	L4	K₃PO₄	DMSO	120	45
5	CuI	L4	K₂CO₃	DMSO	120	25
6	CuI	L4	Cs₂CO₃	DMSO	120	42
7	CuI	L4	K₃PO₄	DMAc	120	18
8	CuI	L4	K₃PO₄	Sulfolane	120	41
9	CuI	L4	K₃PO₄	NMP	120	39
10	CuI	L5	K₃PO₄	DMSO	120	57
11	CuI	L6	K₃PO₄	DMSO	120	23
12	CuI	L5	K₃PO₄	DMSO	130	72 (79)^c
13	CuBr	L5	K₃PO₄	DMSO	130	63
14	Cu₂O	L5	K₃PO₄	DMSO	130	15
15	CuTC	L5	K₃PO₄	DMSO	130	77 (83)^c
16	CuTC	L5	K₃PO₄	DMSO	130	93^d

Entry	Copper salt	Ligand	Base	Solvent	Temp./℃	Yield^b/%
1	CuI	L1	K₃PO₄	DMSO	120	11
2	CuI	L2	K₃PO₄	DMSO	120	12
3	CuI	L3	K₃PO₄	DMSO	120	33
4	CuI	L4	K₃PO₄	DMSO	120	45
5	CuI	L4	K₂CO₃	DMSO	120	25
6	CuI	L4	Cs₂CO₃	DMSO	120	42
7	CuI	L4	K₃PO₄	DMAc	120	18
8	CuI	L4	K₃PO₄	Sulfolane	120	41
9	CuI	L4	K₃PO₄	NMP	120	39
10	CuI	L5	K₃PO₄	DMSO	120	57
11	CuI	L6	K₃PO₄	DMSO	120	23
12	CuI	L5	K₃PO₄	DMSO	130	72 (79)^c
13	CuBr	L5	K₃PO₄	DMSO	130	63
14	Cu₂O	L5	K₃PO₄	DMSO	130	15
15	CuTC	L5	K₃PO₄	DMSO	130	77 (83)^c
16	CuTC	L5	K₃PO₄	DMSO	130	93^d

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碘化亚铜/4-羟基吡啶酰肼催化的(杂)芳基氯代物和苯基亚磺酸钠的偶联反应

CuI/4-Hydroxy Picolinohydrazide Catalyzed Coupling Reaction of (Hetero)aryl Chlorides with Sodium Aryl Sulfinates

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