Three-Component Reaction Involving Alkenes, AgSCF3 and Quinoxalinones Initiated by Trifluoromethylthio Radical

doi:10.6023/cjoc202310002

Abstract

A novel three-component cascade radical reaction involving non-activated olefins, quinoxalin-2(1H)-ones, and AgSCF₃ was proposed. Under the action of the oxidizing agent K₂S₂O₈, 40 quinoxaline derivatives containing SCF₃ were obtained with the highest yield of 78%. This method provides a mild and environmentally friendly approach to prepare trifluoromethylthio-substituted quinoxalines, offering advantages such as high yield, broad substrate scope, atom economy, and environmental efficiency.

Key words: (trifluoromethylthio) silver(I), radical, three-component reaction

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Shenyuan Gao, Haoqiong Zhu, Qiaoling Jin, Lu'er Jin, Xiaozhong Wang, Liyan Dai. Three-Component Reaction Involving Alkenes, AgSCF₃ and Quinoxalinones Initiated by Trifluoromethylthio Radical[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1264-1275.

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References 19

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三氟甲硫基自由基引发涉及烯烃、AgSCF₃和喹喔啉酮的三组分反应

Three-Component Reaction Involving Alkenes, AgSCF₃ and Quinoxalinones Initiated by Trifluoromethylthio Radical

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Enter	Oxidant	Temp./°C	Solvent	Yield^b/%
1	K₂S₂O₈	60	DMSO	30
2	K₂S₂O₈	60	DMSO/H₂O (V∶V=10∶1)	63
3	K₂S₂O₈	60	DMSO/H₂O (V∶V=8∶1)	68
4	K₂S₂O₈	60	DMSO/H₂O (V∶V=6∶1)	71
5	K₂S₂O₈	60	DMSO/H₂O (V∶V=4∶1)	45
6	K₂S₂O₈	60	DMSO/H₂O (V∶V=3∶1)	30
7	K₂S₂O₈	60	DMSO/H₂O (V∶V=2∶1)	21
8	K₂S₂O₈	60	DMSO/H₂O (V∶V=1∶1)	Trace
9	K₂S₂O₈	60	H₂O	Trace
10	K₂S₂O₈	60	CH₂Cl₂/H₂O (V∶V=6∶1)	Trace
11	K₂S₂O₈	60	1,4-Dioxane/H₂O (V∶V=6∶1)	Trace
12	K₂S₂O₈	60	CH₃CN/H₂O (V∶V=6∶1)	52
13	K₂S₂O₈	60	DMF/H₂O (V∶V=6∶1)	Trace
14	K₂S₂O₈	60	THF/H₂O (V∶V=6∶1)	Trace
15	Na₂S₂O₈	60	DMSO/H₂O (V∶V=6∶1)	33
16	(NH₄)₂S₂O₈	60	DMSO/H₂O (V∶V=6∶1)	48
17	TBPB	60	DMSO/H₂O (V∶V=6∶1)	Trace
18	TBHP	60	DMSO/H₂O (V∶V=6∶1)	41
19	DTBP	60	DMSO/H₂O (V∶V=6∶1)	Trace
20^c	K₂S₂O₈	60	DMSO/H₂O (V∶V=6∶1)	56
21^d	K₂S₂O₈	60	DMSO/H₂O (V∶V=6∶1)	73
22	K₂S₂O₈	50	DMSO/H₂O (V∶V=6∶1)	75
23	K₂S₂O₈	40	DMSO/H₂O (V∶V=6∶1)	66
24	K₂S₂O₈	70	DMSO/H₂O (V∶V=6∶1)	63
25^e	K₂S₂O₈	50	DMSO/H₂O (V∶V=6∶1)	42
26		50	DMSO/H₂O (V∶V=6∶1)	Trace
20^c	K₂S₂O₈	60	DMSO/H₂O (V∶V=6∶1)	56

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三氟甲硫基自由基引发涉及烯烃、AgSCF3和喹喔啉酮的三组分反应