I2/叔丁基过氧化氢(TBHP)促进烯烃和N,N-二甲基甲酰胺的氧化-酰胺化反应: 一种制备芳基-α-酮酰胺衍生物的简易方法

doi:10.6023/cjoc202110005

有机化学 ›› 2022, Vol. 42 ›› Issue (5): 1438-1442.DOI: 10.6023/cjoc202110005 上一篇下一篇

研究论文

I₂/叔丁基过氧化氢(TBHP)促进烯烃和N,N-二甲基甲酰胺的氧化-酰胺化反应: 一种制备芳基-α-酮酰胺衍生物的简易方法

肖朵朵^a, 刘海灵^b, 周鹏^a, 张建涛^a^,^*(), 刘卫兵^a^,^*()

a 广东石油化工学院化学学院广东茂名 525000
b 北京师范大学分析测试中心北京 100875

收稿日期:2021-10-05 修回日期:2022-01-17 发布日期:2022-02-10
通讯作者: 张建涛, 刘卫兵
基金资助:
广东省普通高校青年创新基金(2018KQNCX167); 广东石油化工学院人才引进计划(2017rc07); 广东石油化工学院人才引进计划(2019rc048); 广东石油化工学院创新研究团队(519124)

I₂/t-Butylhydroperoxide (TBHP)-Mediated Oxo-amidation of Alkenes with N,N-Dimethylformamide: A Facile Access to Aryl-α-ketoamide Derivatives

Duoduo Xiao^a, Hailing Liu^b, Peng Zhou^a, Jiantao Zhang^a(), Weibing Liu^a()

a College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000
b College Analytical and Testing Centre, Beijing Normal University, Beijing 100875

Received:2021-10-05 Revised:2022-01-17 Published:2022-02-10
Contact: Jiantao Zhang, Weibing Liu
Supported by:
Ordinary University Young Innovative Talents Project of Guangdong Province(2018KQNCX167); Projects of Talents Recruitment of Guangdong University of Petrochemical Technology(2017rc07); Projects of Talents Recruitment of Guangdong University of Petrochemical Technology(2019rc048); Program for Innovative Research Team of Guangdong University of Petrochemical Technology(519124)

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摘要/Abstract

以N,N-二甲基甲酰胺(DMF)为溶剂和二甲胺源, 发展了用于合成芳基-α-酮酰胺衍生物的烯烃双官能化反应. 该过程采用I₂/叔丁基过氧化氢(TBHP)为催化氧化体系, 一系列芳基-α-酮酰胺衍生物以良好的收率合成得到.

关键词: 氧化-酰胺化, 烯烃, N,N-二甲基甲酰胺, 芳基-α-酮酰胺

Difunctionalization of alkenes providing for the synthesis of aryl-α-ketoamide derivatives is developed by using N,N-dimethylformamide (DMF) as the solvent and the source of dimethylamine. This procedure is catalyzed by I₂ and t-butylhydroperoxide (TBHP) as oxidant. A wide range of aryl-α-ketoamide derivatives are generated in good yields.

Key words: oxo-amidation, alkenes, N,N-dimethylformamide, aryl-α-ketoamide

引用此文

肖朵朵, 刘海灵, 周鹏, 张建涛, 刘卫兵. I₂/叔丁基过氧化氢(TBHP)促进烯烃和N,N-二甲基甲酰胺的氧化-酰胺化反应: 一种制备芳基-α-酮酰胺衍生物的简易方法[J]. 有机化学, 2022, 42(5): 1438-1442.

Duoduo Xiao, Hailing Liu, Peng Zhou, Jiantao Zhang, Weibing Liu. I₂/t-Butylhydroperoxide (TBHP)-Mediated Oxo-amidation of Alkenes with N,N-Dimethylformamide: A Facile Access to Aryl-α-ketoamide Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1438-1442.

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图/表 5

Scheme 1. Oxo-amidation protocol for the synthesis of aryl-α- ketoamides from aryl alkenes and DMF

Entry	Peroxide (equiv.)	Base	Solvent	Yield^b/%
1	TBHP (4.0)	Na₂CO₃	DMF	75
2	TBHP (4.0)	NaHCO₃	DMF	72
3	TBHP (4.0)	t-BuOK	DMF	70
4	TBHP (4.0)	Et₃N	DMF	58
5	TBHP (4.0)	DBU	DMF	45
6^c	TBHP (4.0)	Na₂CO₃	Dioxane	30
7	TBHP (6.0)	Na₂CO₃	DMF	88

Table 1. Optimization of reaction conditionsa

Table 2. Substrate scope for the synthesis of aryl-α-ketoamide derivativesa,b

Scheme 2. Possible mechanism for the synthesis of 2a

Scheme 3. Control experiment of intermediate F with TBHP in DMF

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I₂/叔丁基过氧化氢(TBHP)促进烯烃和N,N-二甲基甲酰胺的氧化-酰胺化反应: 一种制备芳基-α-酮酰胺衍生物的简易方法

I₂/t-Butylhydroperoxide (TBHP)-Mediated Oxo-amidation of Alkenes with N,N-Dimethylformamide: A Facile Access to Aryl-α-ketoamide Derivatives

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