钴催化芳基烯烃氧烷基化反应: 快速获得α-烷基取代苯乙酮衍生物

doi:10.6023/cjoc202304010

有机化学 ›› 2023, Vol. 43 ›› Issue (11): 3939-3944.DOI: 10.6023/cjoc202304010 上一篇下一篇

研究论文

钴催化芳基烯烃氧烷基化反应: 快速获得α-烷基取代苯乙酮衍生物

周鹏^a, 朱伟明^a, 张建涛^a^,^b^,^*(), 肖朵朵^a, 郭祥峰^a, 刘卫兵^a^,^*()

a 广东石油化工学院化学学院广东茂名 525000
b 茂名绿色化工研究院广东茂名 525099

收稿日期:2023-04-07 修回日期:2023-06-15 发布日期:2023-07-05
基金资助:
茂名绿色化工研究院“扬帆计划”(MMGCIRI-2022YFJH-Y-037); 茂名市科技计划(2022031); 广东省普通高校重点领域专项(2020-ZDZX2054)

Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives

Peng Zhou^a, Weiming Zhu^a, Jiantao Zhang^a^,^b(), Duoduo Xiao^a, Xiangfeng Guo^a, Weibing Liu^a()

a College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000
b Maoming Green Chemical Industry Research Institute, Maoming, Guangdong 525099

Received:2023-04-07 Revised:2023-06-15 Published:2023-07-05
Contact: * E-mail: zhangjt@gdupt.edu.cn; lwb409@gdupt.edu.cn
Supported by:
Sailing Plan of Maoming Green Chemical Industry Research Institute(MMGCIRI-2022YFJH-Y-037); Science and Technology Planning Project of Maoming City(2022031); Special Projects in Key Fields of Ordinary Universities of Guangdong Province(2020-ZDZX2054)

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摘要/Abstract

烷基芳基酮是化学和生物学中一类有价值的化合物, 被广泛应用于制药、香料、染料、农药、功能材料以及有机合成行业. 发展了钴催化芳基烯烃与叔丁基过氧化氢(TBHP)以及环醚的氧烷基化反应. 该方法适用于各种带有吸电子基团或给电子基团的烯烃底物, 并且以中等产率得到α-烷基取代苯乙酮衍生物. 该方案具有广泛的底物适用范围及灵活性, 在温和条件下即可快速构建一系列增值的苯乙酮衍生物.

关键词: 烷基芳基酮, 钴催化, 氧烷基化, 苯乙酮衍生物

Alkyl aryl ketones are a class of valuable compounds in chemistry and biology, which are widely used in the pharmaceutical, spice, dye, pesticide, functional materials, and organic synthesis industries. A cobalt-catalyzed oxyalkylation reaction of aryl olefin with tert-butyl hydroperoxide (TBHP) and cyclic ethers was developed. Various substrates with electron-withdrawing or electron-donating groups were tolerated in this protocol to provide the α-alkyl substituted aceto- phenones in moderate yields. The present protocol features broad substrate scope, and flexibility, allowing rapid assembly of a series of value-added acetophenone derivatives under mild conditions with good reaction efficacy.

Key words: alkyl aryl ketone, cobalt-catalysis, oxyalkylation, acetophenone derivative

引用此文

周鹏, 朱伟明, 张建涛, 肖朵朵, 郭祥峰, 刘卫兵. 钴催化芳基烯烃氧烷基化反应: 快速获得α-烷基取代苯乙酮衍生物[J]. 有机化学, 2023, 43(11): 3939-3944.

Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo, Weibing Liu. Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3939-3944.

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Entry	[Co]	Base	TBHP/equiv.	Yield^b/%
1	CoCl₂	DMAP	3.0	53
2	Co(acac)₂	DMAP	3.0	43
3	Co(PPh₃)₂Cl₂	DMAP	3.0	50
4	CoBr₂	DMAP	3.0	59
5	CoBr₂	Et₃N	3.0	35
6	CoBr₂	t-BuOK	3.0	0
7	CoBr₂	Na₂CO₃	3.0	12
8	CoBr₂	DBU	3.0	74
9	CoBr₂	DBU	1.0	22
10	CoBr₂	DBU	2.0	55
11	CoBr₂	DBU	4.0	72
12	CoBr₂	DBU	5.0	75
13^c	CoBr₂	DBU	3.0	70
14^d	CoBr₂	DBU	3.0	74
15^e	CoBr₂	DBU	3.0	0
16	—	DBU	3.0	0
17	CoBr₂	—	3.0	8

Entry	[Co]	Base	TBHP/equiv.	Yield^b/%
1	CoCl₂	DMAP	3.0	53
2	Co(acac)₂	DMAP	3.0	43
3	Co(PPh₃)₂Cl₂	DMAP	3.0	50
4	CoBr₂	DMAP	3.0	59
5	CoBr₂	Et₃N	3.0	35
6	CoBr₂	t-BuOK	3.0	0
7	CoBr₂	Na₂CO₃	3.0	12
8	CoBr₂	DBU	3.0	74
9	CoBr₂	DBU	1.0	22
10	CoBr₂	DBU	2.0	55
11	CoBr₂	DBU	4.0	72
12	CoBr₂	DBU	5.0	75
13^c	CoBr₂	DBU	3.0	70
14^d	CoBr₂	DBU	3.0	74
15^e	CoBr₂	DBU	3.0	0
16	—	DBU	3.0	0
17	CoBr₂	—	3.0	8

钴催化芳基烯烃氧烷基化反应: 快速获得α-烷基取代苯乙酮衍生物

Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives

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