Atom Transfer Radical Addition Reactions of Quinoxalin-2(1H)-ones with CBr4 and Styrenes Using Mes-Acr-MeClO4 Photocatalyst DOI

Buddhadeb Pal,

Sathi Sahoo, Prasenjit Mal

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1784 - 1796

Опубликована: Янв. 12, 2024

The atom transfer radical addition (ATRA) reaction is defined as a method for introducing halogenated compounds into alkenes via mechanism. In this study, we present an ATRA approach achieving regioselective functionalization of quinoxalin-2(1H)-ones by activating C–Br bonds CBr4 and subsequent trihaloalkyl-carbofunctionalization styrenes employing the 9-mesityl-10-methylacridinium perchlorate (Fukuzumi) photocatalyst under 3W blue LED (450–470 nm) irradiation. This three-component cascade process demonstrates remarkable efficiency in synthesis 1-methyl-3-(3,3,3-tribromo-1-(4-chlorophenyl)propyl)quinoxalin-2(1H)-one derivatives.

Язык: Английский

Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids under metal-, strong oxidant- and external photocatalyst-free conditions DOI
Long‐Yong Xie,

You-Shu Bai,

Xiang-Qin Xu

и другие.

Green Chemistry, Год журнала: 2020, Номер 22(5), С. 1720 - 1725

Опубликована: Янв. 1, 2020

An eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones and α-oxo carboxylic acids with air as the oxidant under external-photocatalyst-free conditions was established.

Язык: Английский

Процитировано

174

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics DOI

Fukun Cheng,

Lulu Fan, Qi‐Yan Lv

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(20), С. 7971 - 7977

Опубликована: Янв. 1, 2023

Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents for the visible-light-induced 4CzIPN-catalyzed direct C–H alkylation of N -heteroaromatics.

Язык: Английский

Процитировано

51

Visible-light-promoted direct C–H/S–H cross-coupling of quinoxalin-2(1H)-ones with thiols leading to 3-sulfenylated quinoxalin-2(1H)-ones in air DOI
Long‐Yong Xie, Yanling Chen, Qin Li

и другие.

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(24), С. 3950 - 3955

Опубликована: Янв. 1, 2019

A new and efficient visible-light-mediated strategy has been developed for the synthesis of 3-sulfenylated quinoxalin-2(1H)-ones via rhodamine B catalyzed C–H/S–H cross-coupling with thiols in air at room temperature.

Язык: Английский

Процитировано

125

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 DOI
Long‐Yong Xie, Sha Peng, Lihua Yang

и другие.

Green Chemistry, Год журнала: 2020, Номер 23(1), С. 374 - 378

Опубликована: Окт. 23, 2020

Aryl radicals were generated for the first time from aryl acyl peroxides in ethyl acetate under ambient conditions and visible-light illumination absence of any additive, metal catalyst, or external photosensitizer.

Язык: Английский

Процитировано

123

Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones DOI

Pengli Bao,

Fei Liu,

Yufen Lv

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(3), С. 492 - 498

Опубликована: Янв. 1, 2020

Visible-light-mediated procedure has been developed for the synthesis of 3-acyl quinoxalin-2(1H)-ones through acridine red catalyzed decarboxylative acylation α-oxo-carboxylic acids with quinoxalin-2(1H)-ones.

Язык: Английский

Процитировано

120

Photoredox Catalyst Free, Visible Light‐Promoted C3−H Acylation of Quinoxalin‐2(1H)‐ones in Water DOI

Juan Lü,

Xiang‐Kui He,

Xiao Cheng

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(11), С. 2178 - 2182

Опубликована: Фев. 22, 2020

Abstract A method for the synthesis of 3‐acyl quinoxalin‐2(1 H )‐ones through visible‐light promoted decarboxylative acylation α‐oxo‐carboxylic acids with was developed. The reaction performed in aqueous phase and photoredox catalyst not required to run process. magnified image

Язык: Английский

Процитировано

87

Metal-Free Trifluoroalkylation of Quinoxalin-2(1H)-ones with Unactivated Alkenes and Langlois’ Reagent DOI
Na Meng, Leilei Wang, Qishun Liu

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(11), С. 6888 - 6896

Опубликована: Май 11, 2020

A K2S2O8-mediated three-component protocol has been developed for the construction of 3-trifluoroalkylated quinoxalin-2(1H)-ones under metal-free conditions. The present reaction could be accomplished through trifluoroalkylation with unactivated alkenes and Langlois' reagent (CF3SO2Na), which provided a highly attractive approach to access series biologically important quinoxalin-2(1H)-ones.

Язык: Английский

Процитировано

86

Visible-Light-Initiated Cross-Dehydrogenative Coupling of Quinoxalin-2(1H)-ones and Simple Amides with Air as an Oxidant DOI
Long‐Yong Xie,

Jiali Hu,

Yanxi Song

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2019, Номер 7(24), С. 19993 - 19999

Опубликована: Ноя. 8, 2019

By using ambient air as an oxidant, various N-acylated 3-aminoquinoxalin-2(1H)-ones were efficiently synthesized through visible-light-promoted rhodamine B-catalyzed amidation reaction of quinoxalin-2(1H)-ones and amides under metal-free strong oxidant-free conditions.

Язык: Английский

Процитировано

80

A combination of heterogeneous catalysis and photocatalysis for the olefination of quinoxalin-2(1H)-ones with ketones in water: a green and efficient route to (Z)-enaminones DOI
Jun Xu, Lin Huang, Lei He

и другие.

Green Chemistry, Год журнала: 2021, Номер 23(5), С. 2123 - 2129

Опубликована: Янв. 1, 2021

This study describes a novel aqueous reaction for the synthesis of (Z)-enaminones through combination heterogeneous catalysis and photocatalysis.

Язык: Английский

Процитировано

58

Direct para-C–H heteroarylation of anilines with quinoxalinones by metal-free cross-dehydrogenative coupling under an aerobic atmosphere DOI
Jun Xu, Lin Huang, Lei He

и другие.

Green Chemistry, Год журнала: 2021, Номер 23(17), С. 6632 - 6638

Опубликована: Янв. 1, 2021

This study demonstrates a metal-free cross-dehydrogenative coupling for direct para -C–H heteroarylation of anilines with quinoxalinones using air as the sole oxidant and H 2 O/DMSO solvent.

Язык: Английский

Процитировано

58