Palladium-Catalyzed Synthesis of Dihydrofuran-Fused [60]Fullerene Derivatives via Heteroannulation of Olefins

doi:10.6023/cjoc202011015

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2082-2090.DOI: 10.6023/cjoc202011015 Previous Articles Next Articles

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钯催化烯烃杂环化反应制备[60]富勒烯二氢呋喃化合物

朱三娥¹^,^*(), 豆礼锋¹, 张建辉¹, 吴缨¹, 杨伟¹, 鲁红典¹, 卫春祥¹, 邓崇海¹, 董强¹^,^*()

1 合肥学院能源材料与化工学院合肥 230601

收稿日期:2020-11-10 修回日期:2020-12-16 发布日期:2021-02-22
通讯作者: 朱三娥, 董强
基金资助:
国家自然科学基金(21702042); 安徽省高校优秀人才(gxyq2019114); 安徽省高校优秀人才(gxyqZD2019085); 安徽省重点研究与开发计划(201904b11020040)

Palladium-Catalyzed Synthesis of Dihydrofuran-Fused [60]Fullerene Derivatives via Heteroannulation of Olefins

San'e Zhu¹^,^*(), Lifeng Dou¹, Jianhui Zhang¹, Ying Wu¹, Wei Yang¹, Hongdian Lu¹, Chunxiang Wei¹, Chonghai Deng¹, Qiang Dong¹^,^*()

1 School of Energy, Materials and Chemical Engineering, Hefei University, Hefei, Anhui 230601

Received:2020-11-10 Revised:2020-12-16 Published:2021-02-22
Contact: San'e Zhu, Qiang Dong
About author:
* Corresponding authors. E-mail: 18096672005@163.com;
E-mail: qdong@hfuu.edu.cn
Supported by:
National Natural Science Foundation of China(21702042); Program of Anhui Province for Outstanding Talents in University(gxyq2019114); Program of Anhui Province for Outstanding Talents in University(gxyqZD2019085); and the Key Research and Development Project of Anhui Province(201904b11020040)

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Abstract

With the good application prospects in the fields of optoelectronics and medicine, dihydrofuran-fused [60]fullerene derivatives have become a research hot topic in recent years. A series of monosubstituted and disubstituted dihydrofuran-fused [60]fullerene derivatives were synthesized by C—H bond activation and heterocyclic reaction using palladium chloride as catalyst, copper trifluoromethanesulfonate as oxidant, olefins and [60]fullerene as raw materials. The structures of the products were confirmed by¹H NMR, ¹³C NMR, IR and HRMS. The reaction mechanism was studied by designing controlled experiments, and a possible reaction mechanism was proposed.

Key words: olefins, C₆₀, dihydrofuran-fused [60]fullerene, palladium chloride, copper(II) trifluoromethanesulfonate

Cite this article

San'e Zhu, Lifeng Dou, Jianhui Zhang, Ying Wu, Wei Yang, Hongdian Lu, Chunxiang Wei, Chonghai Deng, Qiang Dong. Palladium-Catalyzed Synthesis of Dihydrofuran-Fused [60]Fullerene Derivatives via Heteroannulation of Olefins[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2082-2090.

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References 46

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Entry	Catalyst	Oxidant	Base^b	Acid^c	Yield^d/%
1	Pd(OAc)₂	Cu(OAc)₂	—	—	0
2	Pd(OAc)₂	(NH₄)₂S₂O₈	—	—	0
3	Pd(OAc)₂	K₂S₂O₈	—	—	0
4	Pd(OAc)₂	Oxone	—	—	0
5	Pd(OAc)₂	Ag₂CO₃	—	—	0
6	Pd(OAc)₂	Cu(TFA)₂	—	—	15
7	Pd(OAc)₂	Cu(OTf)₂	—	—	31
8	—	Cu(OTf)₂	—	—	0
9	Pd(TFA)₂	Cu(OTf)₂	—	—	23
10	Pd(CH₃CN)₄(OTf)₂	Cu(OTf)₂	—	—	22
11	PdCl₂	Cu(OTf)₂	—	—	38
12	PdCl₂	Cu(OTf)₂	Na₂CO₃	—	18
13	PdCl₂	Cu(OTf)₂	K₂CO₃	—	29
14	PdCl₂	Cu(OTf)₂	NaOAc?3H₂O	—	23
15	PdCl₂	Cu(OTf)₂	NaHCO₃	—	trace
16	Pd(TFA)₂	Cu(OAc)₂	—	TFA	trace
17	Pd(CH₃CN)₄(OTf)₂	Cu(OAc)₂	—	CF₃SO₃H	23
18	PdCl₂	Cu(OAc)₂	—	CF₃SO₃H	33
19^e	PdCl₂	Cu(OTf)₂	—	—	30
20^f	PdCl₂	Cu(OTf)₂	—	—	11
21^g	PdCl₂	Cu(OTf)₂	—	—	31
22^h	PdCl₂	Cu(OTf)₂	—	—	9
23ⁱ	PdCl₂	Cu(OTf)₂	—	—	0

Entry	Catalyst	Oxidant	Base^b	Acid^c	Yield^d/%
1	Pd(OAc)₂	Cu(OAc)₂	—	—	0
2	Pd(OAc)₂	(NH₄)₂S₂O₈	—	—	0
3	Pd(OAc)₂	K₂S₂O₈	—	—	0
4	Pd(OAc)₂	Oxone	—	—	0
5	Pd(OAc)₂	Ag₂CO₃	—	—	0
6	Pd(OAc)₂	Cu(TFA)₂	—	—	15
7	Pd(OAc)₂	Cu(OTf)₂	—	—	31
8	—	Cu(OTf)₂	—	—	0
9	Pd(TFA)₂	Cu(OTf)₂	—	—	23
10	Pd(CH₃CN)₄(OTf)₂	Cu(OTf)₂	—	—	22
11	PdCl₂	Cu(OTf)₂	—	—	38
12	PdCl₂	Cu(OTf)₂	Na₂CO₃	—	18
13	PdCl₂	Cu(OTf)₂	K₂CO₃	—	29
14	PdCl₂	Cu(OTf)₂	NaOAc?3H₂O	—	23
15	PdCl₂	Cu(OTf)₂	NaHCO₃	—	trace
16	Pd(TFA)₂	Cu(OAc)₂	—	TFA	trace
17	Pd(CH₃CN)₄(OTf)₂	Cu(OAc)₂	—	CF₃SO₃H	23
18	PdCl₂	Cu(OAc)₂	—	CF₃SO₃H	33
19^e	PdCl₂	Cu(OTf)₂	—	—	30
20^f	PdCl₂	Cu(OTf)₂	—	—	11
21^g	PdCl₂	Cu(OTf)₂	—	—	31
22^h	PdCl₂	Cu(OTf)₂	—	—	9
23ⁱ	PdCl₂	Cu(OTf)₂	—	—	0

Substrate 1	Product 2	Substrate 1	Product 2

Substrate 1	Product 2	Substrate 1	Product 2

Substrate 1	Product 2	Substrate 1	Product 2

Substrate 1	Product 2	Substrate 1	Product 2

钯催化烯烃杂环化反应制备[60]富勒烯二氢呋喃化合物

Palladium-Catalyzed Synthesis of Dihydrofuran-Fused [60]Fullerene Derivatives via Heteroannulation of Olefins

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