A Mechanistic Perspective on Photocatalytic EnT-Enabled C3-N-Heteroarylation of Aryl Quinoxaline via C(sp2)–C(sp2) Coupling DOI
Raju Mandal, Subhendu Ghosh,

Sayan Laha

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 11, 2025

An EnT-mediated C3-N-heteroarylation of 2-aryl quinoxalines via decarboxylative radical-radical cross-coupling (C(sp2)-C(sp2)) with oxime esters is presented. Upon photoactivation, the triplet energy photocatalyst transferred to both reacting partners (oxime ester and 2-phenylquinoxaline). The excited undergoes fragmentation a C-centered N-heteroaryl radical an N-centered imine radical. former attacks C3 site quinoxaline diradical, while latter acts as hydrogen atom abstractor (HAA). Computational studies revealed that C-C bond formation heteroaryl energetically more favorable than C-N formation.

Language: Английский

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications DOI
Mingzhu Lu, Jeffrey Goh, Manikantha Maraswami

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(24), P. 17479 - 17646

Published: Oct. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Language: Английский

Citations

155

Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles DOI
Qiong Yan, Xu Wu, Hao Jiang

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 502, P. 215622 - 215622

Published: Dec. 26, 2023

Language: Английский

Citations

79

Recent advances in the transition-metal-free synthesis of quinoxalines DOI Creative Commons
Biplob Borah, L. Raju Chowhan

RSC Advances, Journal Year: 2021, Volume and Issue: 11(59), P. 37325 - 37353

Published: Jan. 1, 2021

Recent advances in the synthesis of quinoxalines under transition metal free conditions are summarized this review article.

Language: Английский

Citations

54

Catalyst-free mechanochemistry as a versatile tool in synthetic chemistry: a review DOI
Bandameeda Ramesh Naidu,

Thondooru Sruthi,

Raghavender Mitty

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(16), P. 6120 - 6148

Published: Jan. 1, 2023

This article presents a review of the reports on catalyst-free mechanochemical organic transformations and ability to initiate reactions that are extremely difficult/impossible occur is notable advancement process.

Language: Английский

Citations

23

Borane‐Catalyzed Tandem Cyclization/Hydrosilylation Towards Enantio‐ and Diastereoselective Construction of trans‐2,3‐Disubstituted‐1,2,3,4‐Tetrahydroquinoxalines DOI

Zhenli Luo,

Zhewei Li, Haoqiang Zhao

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(32)

Published: June 20, 2023

Recent years have witnessed marked progress in the efficient synthesis of various enantioenriched 1,2,3,4-tetrahydroquinoxalines. However, enantio- and diastereoselective access to trans-2,3-disubstituted 1,2,3,4-tetrahydroquinoxalines remains much less explored. Herein we report that a frustrated Lewis pair-based catalyst generated via situ hydroboration 2-vinylnaphthalene with HB(C6 F5 )2 allows for one-pot tandem cyclization/hydrosilylation 1,2-diaminobenzenes 1,2-diketones commercially available PhSiH3 exclusively afford high yields excellent diastereoselectivities (>20 : 1 dr). Furthermore, this reaction can be rendered asymmetric by using an borane-based derived from binaphthyl-based chiral diene give rise almost complete diastereo- enantiocontrol dr, up >99 % ee). A wide substrate scope, good tolerance diverse functionality 20-gram scale production are demonstrated. The diastereocontrol achieved judicious choice borane hydrosilane. catalytic pathway origin stereoselectivity elucidated mechanistic experiments DFT calculations.

Language: Английский

Citations

18

Heterocyclic and heteropolycyclic moieties in organic hole transport materials for perovskite solar cells: Design, synthesis, and performance DOI Creative Commons
Shakil N. Afraj,

Arulmozhi Velusamy,

Ming‐Chou Chen

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 532, P. 216500 - 216500

Published: Feb. 20, 2025

Language: Английский

Citations

1

WEPA: a reusable waste biomass-derived catalyst for external oxidant/metal-free quinoxaline synthesisviatandem condensation–cyclization–oxidation of α-hydroxy ketones DOI
Bandameeda Ramesh Naidu, Katta Venkateswarlu

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(16), P. 6215 - 6223

Published: Jan. 1, 2022

WEPA, a waste biomass-derived catalyst, was used to synthesize quinoxalines from aryl/heteroaryl 1,2-diamines and α-hydroxy ketones via metal catalyst/added oxidant-free sequential condensation–cyclization–oxidation process.

Language: Английский

Citations

27

Mn(I)-Catalyzed Preferential Electrophilic C3-Maleimidation in Quinoxaline Leading to Spirocyclization and Dehydrogenation of Succinimides DOI
Subhendu Ghosh, Tamanna Khandelia, Pritishree Panigrahi

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3806 - 3811

Published: May 17, 2023

A Mn(I)-catalyzed site-selective nondirected C3-maleimidation of quinoxaline is established. Herein, the electrophilic C3-metalation precedes over o-directed strategy to access diversely substituted quinoxaline-appended succinimides. The products undergo PIFA-promoted C(sp2)-C(sp3) spirocyclization via π-electrons drifting from aryls and Selectfluor-mediated dehydrogenation succinimide at room temperature.

Language: Английский

Citations

15

Visible-light-induced organophotocatalytic and singlet oxygen-initiated domino construction of 1,4-dihydropyridines, C-3 functionalized spiro[indoline-3,4′-pyridines] and C-11 functionalized spiro[indeno-[1,2-b]quinoxaline-11,4′-pyridines] DOI
Biplob Borah, Mihir Patat, Vipin Singh

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(7), P. 1518 - 1530

Published: Jan. 1, 2023

A highly efficient pot, atom, and step economical method for the construction of pharmacologically potent structurally functionalized 1,4-dihydropyridines, quaternary centered C-3 spiro[indoline-3,4'-pyridines], C-11 spiro[indeno[1,2-b]quinoxaline-11,4'-pyridines] via rose bengal photoredox catalysis under blue LED irradiation in an aqueous medium at room temperature has been developed. The products were isolated excellent yields within a short reaction time variety functional groups transition metal- ligand-free energy-efficient conditions green solvent system with high mass efficiency process intensity, which are key advantages current work.

Language: Английский

Citations

14

Sustainable approaches towards the synthesis of quinoxalines: An update DOI

Asim Kumar,

Tejas M. Dhameliya, Kirti Rani

et al.

Journal of Molecular Structure, Journal Year: 2022, Volume and Issue: 1259, P. 132732 - 132732

Published: March 2, 2022

Language: Английский

Citations

21