A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H2O-Polyethylene Glycol (PEG-200)

doi:10.6023/cjoc202302030

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3210-3215.DOI: 10.6023/cjoc202302030 Previous Articles Next Articles

水-聚乙二醇(PEG-200)中烯烃与碘代芳烃绿色可循环无负载偶联反应的研究

蒋宜欣^a, 唐伯孝^a^,^b^,^*(), 毛海波^a, 陈雪霞^a, 俞洋杰^a, 全翠英^a, 徐昭阳^a, 石金慧^a, 刘益林^a^,^b^,^*()

a 怀化学院有机合成研究所湖南怀化 418000
b 怀化学院聚乙烯醇纤维材料制备技术湖南省工程实验室湖南怀化 418000

收稿日期:2023-02-28 修回日期:2023-05-08 发布日期:2023-05-29
基金资助:
湖南省自然科学基金(2021JJ30537); 湖南省大学生创新训练基金(S202110548054); 国家自然科学基金(21563015)

A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200)

Yixin Jiang^a, Boxiao Tang^a^,^b(), Haibo Mao^a, Xuexia Chen^a, Yangjie Yu^a, Cuiying Quan^a, Zhaoyang Xu^a, Jinhui Shi^a, Yilin Liu^a^,^b()

a Institute of Organic Synthesis, Huaihua University, Huaihua, Hunan 418000
b Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA) Fiber Material, Huaihua University, Huaihua, Hunan 418000

Received:2023-02-28 Revised:2023-05-08 Published:2023-05-29
Contact: * E-mail: 520tangboxiao@163.com;liuyilinhn@126.com
Supported by:
Natural Science Foundation of Hunan Province(2021JJ30537); University Students Innovation Training Foundation of Hunan Province(S202110548054); National Natural Science Foundation of China(21563015)

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Abstract

By using an environmentally friendly H₂O-polyethylene glycol (PEG-200) system as the reaction medium, a new, green and recyclable protocol was developed for Pd(OAc)₂-catalyzed the cross-coupling reaction of alkenes with aryl iodides. A series of coupling products can be obtained with good selectivity and yield. The Pd(OAc)₂-H₂O-PEG-200 system can be directly recovered and used for more than three cycles without any loss of activity, demonstrating the robustness of the carrier-free palladium catalyst system. As the reaction cost is reduced and the operation is simple, the approach is beneficial to industrial production.

Key words: carrier-free, reusability, H₂O-polyethylene glycol (PEG-200), cross-coupling, green chemistry

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Yixin Jiang, Boxiao Tang, Haibo Mao, Xuexia Chen, Yangjie Yu, Cuiying Quan, Zhaoyang Xu, Jinhui Shi, Yilin Liu. A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200)[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3210-3215.

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Fig. & Tab. 6

Scheme 1. Recyclable carrier Pd-catalyzed Mizoroki-Heck reaction

Scheme 2. Carrier-free Pd(OAc)2-catalyzed Mizoroki-Heck reaction in the green recyclable systems

Entry	Temp./℃	Base	V(H₂O)∶V(PEG-200)	Yield^b/%
1	60	—	1∶1	<5
2	60	NEt₃	1∶1	46
3	60	NaHCO₃	1∶1	76
4	60	NaOAc	1∶1	21
5	60	NaOH	1∶1	58
6	60	Cs₂CO₃	1∶1	93
7	60	K₂CO₃	1∶1	96
8^c	60	K₂CO₃	1∶1	94
9^d	60	K₂CO₃	1∶1	80
10	80	K₂CO₃	1∶1	92
11	40	K₂CO₃	1∶1	31
12	60	K₂CO₃	3∶7	88
13	60	K₂CO₃	7∶3	45

Table 1. Coupling reaction between iodobenzene and tert-butyl acrylate in H2O/PEG-200

Table 2. Coupling reaction between aryl iodides and tert-butyl acrylate in H2O/PEG-200

Table 3. Coupling reaction between aryl iodides and alkenes in H2O/PEG-200

Scheme 3. Amplification experiment for Mizoroki-heck reaction

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水-聚乙二醇(PEG-200)中烯烃与碘代芳烃绿色可循环无负载偶联反应的研究

A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200)

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References 31

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