CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals DOI
Alexander S. Budnikov, Igor B. Krylov, Olga M. Mulina

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1714 - 1755

Опубликована: Апрель 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

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

124

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

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

88

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

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