Palladium-Catalyzed Reductive Cross-Coupling of Propargyl Acetates with Aryl Iodides Involving the Insertion of SO2

doi:10.6023/cjoc202312010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 2033-2040.DOI: 10.6023/cjoc202312010 Previous Articles Next Articles

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钯催化SO₂插入的炔丙基乙酸酯和碘代芳烃的还原偶联反应

张倩, 应垚璐, 张泓银, 徐林博, 林新奎, 黄晓雷^*()

浙江师范大学化学与材料科学学院先进催化材料教育部重点实验室浙江金华 321004

收稿日期:2023-12-09 修回日期:2024-01-23 发布日期:2024-02-19
基金资助:
国家自然科学基金(22101259); 浙江省自然科学基金(LQ22B020002)

Palladium-Catalyzed Reductive Cross-Coupling of Propargyl Acetates with Aryl Iodides Involving the Insertion of SO₂

Qian Zhang, Yaolu Ying, Hongyin Zhang, Linbo Xu, Xinkui Lin, Xiaolei Huang^*()

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang 321004

Received:2023-12-09 Revised:2024-01-23 Published:2024-02-19
Contact: * E-mail: huangxl@zjnu.edu.cn
Supported by:
National Natural Science Foundation of China(22101259); Zhejiang Provincial Natural Science Foundation(LQ22B020002)

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Abstract

An efficient palladium-catalyzed reductive cross-coupling of propargyl acetates with aryl iodides involving the insertion of sulfur dioxide has been reported. This method employs 1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate (DABSO) as SO₂ surrogate, reductive manganese powder as reductant, and features mild reaction conditions, broad substrate scope and good functional group tolerance.

Key words: palladium-catalysis, reductive cross-coupling, propargyl acetates, sulfur dioxide

Cite this article

Qian Zhang, Yaolu Ying, Hongyin Zhang, Linbo Xu, Xinkui Lin, Xiaolei Huang. Palladium-Catalyzed Reductive Cross-Coupling of Propargyl Acetates with Aryl Iodides Involving the Insertion of SO₂[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 2033-2040.

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References 15

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Entry	SO₂ surrogate	Reductive metal	Solvent	Yield^b/%
1	DABSO	Zn	DMSO	46
2	DABSO	Sn	DMSO	0
3	DABSO	Mn	DMSO	84
4	DABSO	Mg	DMSO	0
5	DABSO	Fe	DMSO	27
6	Na₂S₂O₅	Mn	DMSO	26
7	K₂S₂O₅	Mn	DMSO	10
8	Na₂S₂O₄	Mn	DMSO	0
9	DABSO	Mn	DMF	14
10	DABSO	Mn	DCE	Trace
11	DABSO	Mn	PhMe	0
12	DABSO	Mn	THF	0
13	DABSO	Mn	MeCN	0

Entry	SO₂ surrogate	Reductive metal	Solvent	Yield^b/%
1	DABSO	Zn	DMSO	46
2	DABSO	Sn	DMSO	0
3	DABSO	Mn	DMSO	84
4	DABSO	Mg	DMSO	0
5	DABSO	Fe	DMSO	27
6	Na₂S₂O₅	Mn	DMSO	26
7	K₂S₂O₅	Mn	DMSO	10
8	Na₂S₂O₄	Mn	DMSO	0
9	DABSO	Mn	DMF	14
10	DABSO	Mn	DCE	Trace
11	DABSO	Mn	PhMe	0
12	DABSO	Mn	THF	0
13	DABSO	Mn	MeCN	0

钯催化SO₂插入的炔丙基乙酸酯和碘代芳烃的还原偶联反应

Palladium-Catalyzed Reductive Cross-Coupling of Propargyl Acetates with Aryl Iodides Involving the Insertion of SO₂

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钯催化SO2插入的炔丙基乙酸酯和碘代芳烃的还原偶联反应