Visible-light-induced cascade reaction: a sustainable approach towards molecular complexity DOI
Sumit Ghosh, Pranjal Pyne,

Anogh Ghosh

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(8), С. 1591 - 1628

Опубликована: Янв. 1, 2023

Photoredox catalysis has demonstrated rapid evolution in the field of synthetic organic chemistry. On other hand, splendour cascade reactions providing complex molecular architectures renders them a cutting-edge research area. Therefore, merging photocatalysis with synthesis brings out paradigm immense potential. The development photocascade for target molecule particular skeleton and stereochemical framework presents certain challenges but provides robust environmentally benign alternative. This comprehensive review assembles all accomplishments highlights visible-light-induced literature coverage up to October 2022.

Язык: Английский

Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: synthesis of quinazolinones containing the CF2R group DOI

Jin Wook Yang,

Bin Sun, Hao Ding

и другие.

Green Chemistry, Год журнала: 2020, Номер 23(1), С. 575 - 581

Опубликована: Дек. 10, 2020

A photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed.

Язык: Английский

Процитировано

92

Hypervalent Iodine(III)‐Promoted Rapid Cascade Reaction of Quinoxalinones with Unactivated Alkenes and TMSN3 DOI
Jiabin Shen, Jun Xu, Lin Huang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2019, Номер 362(1), С. 230 - 241

Опубликована: Ноя. 15, 2019

Abstract The first example of rapidly three‐component cascade reaction quinoxalinones with unactivated alkenes and TMSN 3 under mild condition has been described. This approach provides a practical solution for the rapid modification enables new planning strategies synthesis bioactive organoazides. A radical mechanism is responsible this transformation. magnified image

Язык: Английский

Процитировано

85

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

85

Recent Advances in Photocatalytic Functionalization of Quinoxalin‐2‐ones DOI
Jaume Rostoll‐Berenguer, Gonzalo Blay, José R. Pedro

и другие.

European Journal of Organic Chemistry, Год журнала: 2020, Номер 2020(39), С. 6148 - 6172

Опубликована: Июнь 23, 2020

Visible‐light‐mediated chemical reactions have become highly popular in the last ten years. This review covers recent developments visible‐light photofunctionalization of quinoxalin‐2‐one derivatives. Reaction types been categorized depending on kind bond formed: C–C, C–O, C–N, C–S, C–P, and C–X, with representative examples discussion catalyst used providing insightful mechanistic details. Moreover, their applications to synthesis biologically active compounds has also discussed.

Язык: Английский

Процитировано

85

Metal-Free Activation of C–I Bonds and Perfluoroalkylation of Alkenes with Visible Light Using Phosphine Catalysts DOI

Lucas Helmecke,

Michael Spittler,

Kai D. Baumgarten

и другие.

Organic Letters, Год журнала: 2019, Номер 21(19), С. 7823 - 7827

Опубликована: Сен. 18, 2019

An efficient metal-free, photomediated iodo perfluoroalkylation under mild conditions was developed. Using catalytic amounts (10 mol %) of phosphines and blue light irradiation, various olefins are transformed into the corresponding addition products within short reaction times. For this purpose, a modular convenient 3D printed photoreactor constructed, which is presented as an open source model. The presumably proceeds upon generation perfluoroalkyl radicals, formed by catalyst-induced absorption enhancement.

Язык: Английский

Процитировано

82

Nickel-catalyzed electrochemical reductive decarboxylative coupling of N-hydroxyphthalimide esters with quinoxalinones DOI

Fei Lian,

Kun Xu, Wei Meng

и другие.

Chemical Communications, Год журнала: 2019, Номер 55(97), С. 14685 - 14688

Опубликована: Янв. 1, 2019

The first example of electrochemically enabled, NiCl2-catalyzed reductive decarboxylative coupling N-hydroxyphthalimide esters with quinoxalinones was developed.

Язык: Английский

Процитировано

81

A general and green fluoroalkylation reaction promoted via noncovalent interactions between acetone and fluoroalkyl iodides DOI
Ting Mao,

Ming-Jian Ma,

Liang Zhao

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(12), С. 1815 - 1818

Опубликована: Янв. 1, 2020

The first example of visible light promoted fluoroalkylation reactions initiated via noncovalent interactions between acetone and fluoroalkyl iodides is presented. reaction system features synthetic simplicity, mild conditions without any photoredox catalyst, high functional group tolerance. A wide range substrate scopes such as alkenes, alkynes (hetero)arenes were all compatible with the system.

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

57

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

57

Photoinduced Three-Component Difluoroalkylation of Quinoxalinones with Alkenes via Difluoroiodane(III) Reagents DOI

Ningning Zhou,

Ruiyue Liu,

Chunmeng Zhang

и другие.

Organic Letters, Год журнала: 2022, Номер 24(19), С. 3576 - 3581

Опубликована: Май 12, 2022

An environmentally friendly strategy for the photocatalyzed three-component reaction between quinoxalinones, alkenes, and hypervalent iodine(III) reagents is disclosed. The new designed difluoroiodane(III) reagent shows excellent reactivity, providing a wide range of difluoroalkyl-substituted quinoxaline-2(1H)-ones in moderate to yields under mild conditions. Experimental studies demonstrated that difluoroalkyl radical intermediate was involved this reaction.

Язык: Английский

Процитировано

48