Benzylic Oxidation Catalyzed by Cobalt(II)-Terpyridine Coordination Polymers

doi:10.6023/cjoc202104028

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4409-4414.DOI: 10.6023/cjoc202104028 Previous Articles Next Articles

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钴(II)-三联吡啶配位聚合物催化的苄位直接氧化

刘建奇, 范伟伟^*(), 熊航行, 江京耘, 詹红菊

荆楚理工学院化工与药学院湖北荆门 448000

收稿日期:2021-04-14 修回日期:2021-06-10 发布日期:2021-08-09
通讯作者: 范伟伟
基金资助:
湖北省科技创新群体项目(T2020023); 荆门市科技计划(2020ZDYF002)

Benzylic Oxidation Catalyzed by Cobalt(II)-Terpyridine Coordination Polymers

Jianqi Liu, Weiwei Fan(), Hangxing Xiong, Jingyun Jiang, Hongju Zhan

College of Chemical Engineering and Pharmacy, Jingchu University of Technology, Jingmen, Hubei 448000

Received:2021-04-14 Revised:2021-06-10 Published:2021-08-09
Contact: Weiwei Fan
Supported by:
Hubei Provincial Scientific and Technological Innovation Team Project(T2020023); Science and Technology Plan Project of Jingmen City(2020ZDYF002)

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Abstract

Direct benzylic C—H oxidation for the synthesis of aromatic ketones was developed. Employing cobalt(II)-terpyridine coordination polymers as catalyst, tert-butyl hydroperoxide (TBHP) as oxidant and Na₂CO₃ as activator, 19 aromatic ketones were prepared with good to excellent yields (78%~99%) in water. The reaction showed a broad range of substrates with good functional group tolerance and chemical selectivity. By control experiments, a trapping experiment using 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and detection of intermediates during reaction, a reasonable radical mechanism for this type of reaction was also demonstrated.

Key words: direct benzylic oxidation, coordination polymer, tert-butyl hydroperoxide, ketone

Cite this article

Jianqi Liu, Weiwei Fan, Hangxing Xiong, Jingyun Jiang, Hongju Zhan. Benzylic Oxidation Catalyzed by Cobalt(II)-Terpyridine Coordination Polymers[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4409-4414.

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钴(II)-三联吡啶配位聚合物催化的苄位直接氧化

Benzylic Oxidation Catalyzed by Cobalt(II)-Terpyridine Coordination Polymers

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Entry	Catalyst	Oxidant	Activator	Solvent	Time/h	Yield^b/%
1	1	TBHP	Na₂CO₃	H₂O	7	>99
2	—	TBHP	Na₂CO₃	H₂O	10	—
3	CoCl₂•6H₂O	TBHP	Na₂CO₃	H₂O	10	35
4	1	—	Na₂CO₃	H₂O	10	—
5	1	O₂^c	Na₂CO₃	H₂O	10	—
6	1	H₂O₂	Na₂CO₃	H₂O	10	—
7	1	^tBuOO^tBu	Na₂CO₃	H₂O	10	—
8	1	TBHP	Na₂CO₃	MeCN	10	62
9	1	TBHP	Na₂CO₃	MeOH	10	33
10	1	TBHP	Na₂CO₃	Dioxane	10	6
11	1	TBHP	Na₂CO₃	EtOH	10	11
12	1	TBHP	—	H₂O	7	13
13	1	TBHP	K₂CO₃	H₂O	7	>99
14	1	TBHP	NaOH	H₂O	7	>99
15	1	TBHP	Et₃N	H₂O	7	>99
16	1	TBHP	^tBuOK	H₂O	7	90

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