Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines

doi:10.6023/cjoc202209020

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1492-1498.DOI: 10.6023/cjoc202209020 Previous Articles Next Articles

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铜催化亚砜叶立德与邻苯二胺[4＋2]环加成反应

李春生^*(), 连晓琪, 陈莲芬^*()

肇庆学院环境与化学工程学院广东肇庆 526061

收稿日期:2022-09-16 修回日期:2022-10-23 发布日期:2022-12-07
通讯作者: 李春生, 陈莲芬
基金资助:
国家自然科学基金(22002139); 广东省基础与应用基础研究基金(2019A1515110550); 广东省基础与应用基础研究基金(2020A1515111156); 广东省普通高校青年创新人才类项目(2019KQNCX174); 广东省普通高校青年创新人才类项目(2020KQNCX096); 肇庆学院科研基金(202013); 大学生创新创业训练计划(202110580015)

Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines

Chunsheng Li(), Xiaoqi Lian, Lianfen Chen()

School of Environmental and Chemical Engineering, Zhaoqing University, Zhaoqing, Guangdong 526061

Received:2022-09-16 Revised:2022-10-23 Published:2022-12-07
Contact: Chunsheng Li, Lianfen Chen
Supported by:
National Natural Science Foundation of China(22002139); Guangdong Basic and Applied Basic Research Foundation(2019A1515110550); Guangdong Basic and Applied Basic Research Foundation(2020A1515111156); Young Innovative Talents Project of General Colleges and Universities in Guangdong Province(2019KQNCX174); Young Innovative Talents Project of General Colleges and Universities in Guangdong Province(2020KQNCX096); Research Foundation of Zhaoqing University(202013); College Students’ Innovation and Entrepreneurship Training Program(202110580015)

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Abstract

Herein, a novel [4＋2] annulation of a wide range of sulfoxonium ylides and o-phenylenediamines was reported, which was catalyzed by cheap and commercially available copper catalyst. The research results indicated that under the optimal reaction conditions, the isolated yield was up to 93% with 10 mol% Cu(OAc)₂ as catalyst, 1.0 equiv. of NaOAc as additive and 1,2-dichloroethane (DCE) as solvent at 80 ℃ for 24 h. This method features cheap and commerial available catalyst, mild reaction conditions, broad substrate scope and excellent functional groups tolerance.

Key words: copper catalysis, [4＋2] annulations, sulfoxonium ylides, quinoxaline

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Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498.

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铜催化亚砜叶立德与邻苯二胺[4＋2]环加成反应

Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines

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Entry	Catalyst	Additive	Solvent	Yield^b/%
1	Pd(OAc)₂	CsOAc	DCE	0
2	[Ir(cod)Cl]₂	CsOAc	DCE	60
3	(Cp*RhCl₂)₂	CsOAc	DCE	58
4	Cu(OAc)₂	CsOAc	DCE	54
5	Cu(OAc)₂	NaOAc	DCE	85
6	Cu(OAc)₂	KOAc	DCE	62
7	Cu(OAc)₂	NaHCO₃	DCE	43
8	Cu(OAc)₂	Na₂CO₃	DCE	30
9	Cu(OAc)₂	NaOAc	DCM	35
10	Cu(OAc)₂	NaOAc	MeCN	42
11	Cu(OAc)₂	NaOAc	THF	50
12	Cu(OAc)₂	NaOAc	Toluene	58
13	Cu(OAc)₂	NaOAc	Dioxane	38
14	—	CsOAc	DCE	0
15^c	Cu(OAc)₂	NaOAc	DCE	93
16^d	Cu(OAc)₂	NaOAc	DCE	80
17^e	Cu(OAc)₂	NaOAc	DCE	95
18^f	Cu(OAc)₂	NaOAc	DCE	24

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