Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction

doi:10.6023/cjoc202112018

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1443-1452.DOI: 10.6023/cjoc202112018 Previous Articles Next Articles

ARTICLES

可见光诱导无金属条件下交叉脱氢偶联反应合成醌类苄基化衍生物

王馨瑶^a^,^b, 张晴晴^a, 刘书扬^a, 李敏^b^,^*(), 李海芳^c^,^*(), 段春迎^a^,^b, 金云鹤^a^,^*()

a 大连理工大学张大煜学院辽宁大连 116024
b 大连理工大学化工学院精细化工国家重点实验室辽宁大连 116024
c 清华大学化学系生命有机磷化学及化学生物学教育部重点实验室北京 100084

收稿日期:2021-12-13 修回日期:2022-01-26 发布日期:2022-02-10
通讯作者: 李敏, 李海芳, 金云鹤
基金资助:
国家自然科学基金(21901032); 国家自然科学基金(21775086); 中央高校基本科研业务费(DUT21LK13)

Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction

Xinyao Wang^a^,^b, Qingqing Zhang^a, Shuyang Liu^a, Min Li^b(), Haifang Li^c(), Chunying Duan^a^,^b, Yunhe Jin^a()

a Zhang Dayu School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024
b State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, Liaoning 116024
c Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, 100084

Received:2021-12-13 Revised:2022-01-26 Published:2022-02-10
Contact: Min Li, Haifang Li, Yunhe Jin
Supported by:
National Natural Science Foundation of China(21901032); National Natural Science Foundation of China(21775086); Fundamental Research Funds for the Central Universities(DUT21LK13)

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Abstract

Benzylated quinones widely exist in natural products and drug molecules. Thus their convenient synthesis with high efficiency brings great significance. However, hard conditions are still essential among the present reports. Herein, the development of visible light-induced metal-free benzylation of quinones via cross dehydrogenation coupling reaction with methylene blue as photocatalyst, tert-butyl hydroperoxide as oxidant, and toluene derivatives as benzylation reagent is reported. The reaction exhibits many advantages, including mild conditions, a broad scope with good functional group tolerance, low cost, and avoidance of metal remaining in products. This method may bring novel inspiration and approach for synthesis of bioactive quinones.

Key words: visible light-induced, metal-free synthesis, cross dehydrogenation coupling, C—H activation, quinones, benzylation

Cite this article

Xinyao Wang, Qingqing Zhang, Shuyang Liu, Min Li, Haifang Li, Chunying Duan, Yunhe Jin. Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1443-1452.

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Fig. & Tab. 6

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Entry	Catalyst	Oxidant	Solvent
1	fac-Ir(ppy)₃	TBHP	CH₂Cl₂	61
2	Ir(ppy)₂(dtbbpy)(PF₆)	TBHP	CH₂Cl₂	44
3	Ru(bpy)₃Cl₂	TBHP	CH₂Cl₂	26
4	Eosin Y	TBHP	CH₂Cl₂	Trace
5	MB	TBHP	CH₂Cl₂	84
6	MB	TBHP	CH₃CN	29
7	MB	TBHP	DMF	Trace
8	MB	TBHP	THF	0
9	MB	TBHP	MeOH	Trace
10	MB	TBHP	DCE	8
11	MB	TBHP	CCl₄	21
12	MB	TBPB	CH₂Cl₂	36
13	MB	H₂O₂	CH₂Cl₂	Trace
14	MB	(NH₄)₂S₂O₈	CH₂Cl₂	54
15	MB	K₂S₂O₈	CH₂Cl₂	48
16^c	MB	—	CH₂Cl₂	15
17^d	MB	—	CH₂Cl₂	12
18	—	TBHP	CH₂Cl₂	0
19^e	MB	TBHP	CH₂Cl₂	58
20^f	MB	TBHP	CH₂Cl₂	0

Entry	Catalyst	Oxidant	Solvent
1	fac-Ir(ppy)₃	TBHP	CH₂Cl₂	61
2	Ir(ppy)₂(dtbbpy)(PF₆)	TBHP	CH₂Cl₂	44
3	Ru(bpy)₃Cl₂	TBHP	CH₂Cl₂	26
4	Eosin Y	TBHP	CH₂Cl₂	Trace
5	MB	TBHP	CH₂Cl₂	84
6	MB	TBHP	CH₃CN	29
7	MB	TBHP	DMF	Trace
8	MB	TBHP	THF	0
9	MB	TBHP	MeOH	Trace
10	MB	TBHP	DCE	8
11	MB	TBHP	CCl₄	21
12	MB	TBPB	CH₂Cl₂	36
13	MB	H₂O₂	CH₂Cl₂	Trace
14	MB	(NH₄)₂S₂O₈	CH₂Cl₂	54
15	MB	K₂S₂O₈	CH₂Cl₂	48
16^c	MB	—	CH₂Cl₂	15
17^d	MB	—	CH₂Cl₂	12
18	—	TBHP	CH₂Cl₂	0
19^e	MB	TBHP	CH₂Cl₂	58
20^f	MB	TBHP	CH₂Cl₂	0

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可见光诱导无金属条件下交叉脱氢偶联反应合成醌类苄基化衍生物

Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction

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