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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1714 - 1755

Published: April 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.

Language: 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

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(5), P. 1720 - 1725

Published: Jan. 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.

Language: Английский

Citations

174

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

Fukun Cheng,

Lulu Fan, Qi‐Yan Lv

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7971 - 7977

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Organic Chemistry Frontiers, Journal Year: 2019, Volume and Issue: 6(24), P. 3950 - 3955

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 23(1), P. 374 - 378

Published: Oct. 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.

Language: Английский

Citations

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

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(3), P. 492 - 498

Published: Jan. 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.

Language: Английский

Citations

120

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

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(11), P. 6888 - 6896

Published: May 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.

Language: Английский

Citations

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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(11), P. 2178 - 2182

Published: Feb. 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

Language: Английский

Citations

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

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2019, Volume and Issue: 7(24), P. 19993 - 19999

Published: Nov. 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.

Language: Английский

Citations

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

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(5), P. 2123 - 2129

Published: Jan. 1, 2021

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

Language: Английский

Citations

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

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(17), P. 6632 - 6638

Published: Jan. 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.

Language: Английский

Citations

58