Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1<i>H</i>)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions

Xie, Long‐Yong; Peng, Sha; Yang, Lihua; Peng, Cun; Lin, Ying‐Wu; Yu, Xianyong; Cao, Zhong; Peng, Yu‐Yu; He, Wei‐Min

doi:10.1039/d0gc02844d

Cited by 115 publications

(38 citation statements)

References 79 publications

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“…Therefore, the exploration of C–H aminomethylation of quinoxalin-2(1 H )-ones with N -methylanilines is still meaningful and challenging. Over the past years, the visible-light-induced cross-dehydrogenative coupling (CDC) reaction has emerged as a popular and ideal strategy for the step- and atom-economical construction of C–C bonds due to the advantages such as high efficiency, mild reaction conditions, and low energy consumption . Herein, we disclose the first visible-light-induced CDC reactions of N -heterocycles including 1,2,4-triazine-3,5(2 H ,4 H )-diones and quinoxalin-2(1 H )-ones with N -methylanilines (Scheme , equation e).…”

Section: Introductionmentioning

confidence: 87%

Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Zhang

Chen

et al. 2021

J. Org. Chem.

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Disclosed herein is a cross-dehydrogenative-coupling reaction of N-heterocycles including 1,2,4-triazine-3,5(2H, 4H)-diones and quinoxaline-2(1H)-ones with N-methylanilines to form C(sp 2 )−C(sp 3 ) under visible-light illumination and ambient air at room temperature. In this process, easily available Ru(bpy) 3 Cl 2 •6H 2 O serves as the catalyst, and air acts as the green oxidant. This method features high atom economy, environmental friendliness, and convenient operation and provides an efficient and practical access to aminomethyl-substituted Nheterocycles with extensive functional group compatibility in 40− 86% yields.

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Section: Introductionmentioning

confidence: 87%

Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Zhang

Chen

et al. 2021

J. Org. Chem.

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“…自由基机理, 与魏伟等 [29] 报道的机理类似. 2021 年, 何卫民等 [32] 首次在没有金属氧化剂、外部氧化剂及外部光敏剂存在及可见光照射下, 以乙酸乙酯为溶剂, 首次实现了喹喔啉-2(1H)-酮 1 与芳基酰基过氧化物 81 的脱羧芳基化反应(Scheme 24). 该反应具有良好的化学选择性和区域选择性, 氮上含有不同链长的烷基或苯基的喹喔啉-2(1H)-酮均能有效地参与该反应, 并获得不错的收率.…”

Section: 同年何卫民等unclassified

Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one

Liu¹,

Li²,

Zhuang³

et al. 2021

Chinese Journal of Organic Chemistry

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Quinoxalin-2(1H)-ones are a kind of important nitrogen-containing heterocyclic compounds, which have strong biological activity and chemical properties, and play an important role in synthesis chemistry, functional materials, drugs and so on. In recent years, the construction of 3-functionalized quinoxalin-2(1H)-one by C-H functionalization has attracted the attention of many scholars and made important progress. Among them, green chemistry oriented photocatalysis and electrochemical synthesis are becoming powerful tools for C-H functionalization of quinoxaline-2(1H)-one. In view of the great influence of photochemistry in synthetic chemistry, the research status of C-H functionalization of quinoxaline-2(1H)-one in visible light catalysis and electrochemical synthesis is summarized, hoping to promote the further development of green synthesis strategy in the functionalization of nitrogen-containing heterocycles. Keywords quinoxalin-2(1H)-one; visible-light; electrochemistry; C-H functionalization 喹喔啉-2(1H)-酮作为一种重要的含氮杂环单元, 具有很强的生物活性与优异的化学特性, 并背被泛应用于合成化学、材料、天然产物和药物工业领域 [1] . 其中, 3-取代的喹喔啉酮-2(1H)-酮表现出独特特性和生物活性, 常被开发成潜在的强效药物, 如抗肿瘤药、抗糖尿病药、抗炎药、减肥药及心血管药等 [2] (图 1). 近年来, 喹喔啉-键、C-O 键、C-N 键、C-S 键、C-P 键等), 从而实现喹喔啉-2(1H)-酮的烷基化、芳基化、酰基化、三氟甲基化、烷氧基化、亚磺酰化、硅烷化、磷酸化和醚化等 (Scheme 1) [4] .

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“…As a part of our continuing interest in functionalized quinoxalines [ 30 , 37 , 85 , 86 ], herein, we wish to report sunlight induced and g-C 3 N 4 catalyzed sulfenylation of quinoxalin-2(1 H )-ones under air conditions ( Scheme 1 d). The current reaction provides a highly attractive and practical approach to selectively access various 3-sulfenylated quinoxalin-2(1 H )-ones in good to excellent yields.…”

Section: Introductionmentioning

confidence: 99%

Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones

et al. 2022

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A sunlight-promoted sulfenylation of quinoxalin-2(1H)-ones using recyclable graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst was developed. Using the method, various 3-sulfenylated quinoxalin-2(1H)-ones were obtained in good to excellent yields under an ambient air atmosphere. Moreover, the heterogeneous catalyst can be recycled at least six times without significant loss of activity.

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Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions

Abstract: Aryl radicals were generated for the first time from the cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate at ambient conditions under visible-light illumination in the absence...

Cited by 115 publications

References 79 publications

Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one

Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones

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Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions

Abstract: Aryl radicals were generated for the first time from the cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate at ambient conditions under visible-light illumination in the absence...

Cited by 115 publications

References 79 publications

Visible-Light-Induced C(sp2)–C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Visible-Light-Induced C(sp2)–C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one

Sunlight Induced and Recyclable g-C3N4 Catalyzed C-H Sulfenylation of Quinoxalin-2(1H)-Ones

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Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions

Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl-N-methylanilines under Mild Conditions