Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts DOI

Sudip Sau,

Shinobu Takizawa, Hun Young Kim

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8821 - 8826

Published: Oct. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Language: Английский

Double Strain-Release [2π+2σ]-Photocycloaddition DOI
Subhabrata Dutta, Yilin Lu, Johannes E. Erchinger

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(8), P. 5232 - 5241

Published: Feb. 13, 2024

In pursuit of potent pharmaceutical candidates and to further improve their chemical traits, small ring systems can serve as a potential starting point. Small units have the additional merit loaded strain at core, making them suitable reactants they capitalize on this intrinsic driving force. With introduction cyclobutenone strained precursor ketene, photocycloaddition with another unit, bicyclo[1.1.0]butane (BCB), enables reactivity both π-units in transient ketene. This double strain-release driven [2π+2σ]-photocycloaddition promotes synthesis diverse heterobicyclo[2.1.1]hexane units, pharmaceutically relevant bioisostere. The effective under catalyst-free conditions high functional group tolerance defines its synthetic utility. Experimental mechanistic studies density theory (DFT) calculations suggest that takes place via triplet mechanism.

Language: Английский

Citations

40

Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles in a sustainable solvent DOI

Fan‐Lin Zeng,

Kunchen Xie,

Yuting Liu

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(4), P. 1732 - 1737

Published: Jan. 1, 2022

A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocyclesunder air and room temperature conditions.

Language: Английский

Citations

54

Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes DOI Creative Commons

Amanda Bunyamin,

Carol Hua, Anastasios Polyzos

et al.

Chemical Science, Journal Year: 2022, Volume and Issue: 13(11), P. 3273 - 3280

Published: Jan. 1, 2022

Visible light induced singlet nucleophilic carbenes undergo rapid [2 + 1]-cycloaddition with tethered olefins to afford unique bicyclo[3.1.0]hexane and bicyclo[4.1.0]heptane scaffolds. This cyclopropanation process requires only visible irradiation proceed, circumventing the use of exogenous (photo)catalysts, sensitisers or additives showcases a vastly underexplored mode reactivity for in chemical synthesis. The discovery additional transformations including cyclopropanation/retro-Michael/Michael cascade chromanones photochemical C-H insertion reaction are also described.

Language: Английский

Citations

49

Nanoarchitecting a Dual Z-Scheme Zr-MOF/Ti-MOF/g-C3N4 Heterojunction for Boosting Gomberg–Buchmann–Hey Reactions under Visible Light Conditions DOI

Hassan Sepehrmansourie,

Hassan Alamgholiloo, Mohammad Ali Zolfigol

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(8), P. 3182 - 3193

Published: Feb. 13, 2023

Combining more than two metal–organic frameworks (MOFs) with different structures is an intelligent strategy for the architecture of hybrid MOFs. Herein, well-organized UiO-66(Zr)-on-MIL-125(Ti)-NH2 growth g-C3N4 nanosheets was developed Gomberg–Buchmann–Hey reaction under visible light irradiation (λ > 420 nm). First, UiO-66(Zr) micropores as host MOFs were fabricated by a solvothermal method. Subsequently, MIL-125(Ti)-NH2 crystals and grown inside to obtain new type dual Z-scheme Zr-MOF/Ti-MOF/g-C3N4 heterojunction photocatalyst. Under irradiation, this acts highly efficient photocatalyst forming C–C bonds via diazonium salts, which can compete best systems. The findings indicated that presence Zr Ti metals in MOF-on-MOF could significantly increase separation photogenerated electron–hole pairs then enhance photocatalytic performance. present study not only provides insights into on other but also develops materials coupling reactions organic irradiation.

Language: Английский

Citations

33

Phototriggered Self-Catalyzed Phosphorylation of 3,4-Dihydroquinoxalin-2(1H)-ones with Diarylphosphine Oxides in EtOH DOI
Yanfang Jiang, Wen‐Tao Ouyang,

Hong‐Tao Ji

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 19, 2024

A highly effective external photocatalyst- and additive-free method for the phosphorylation of 3,4-dihydroquinoxalin-2(1

Language: Английский

Citations

12

Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates DOI Creative Commons

Daksh Singh Davas,

Dinesh Kumar Gopalakrishnan,

Sandeep Kumar

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(3), P. 1073 - 1080

Published: March 1, 2024

Herein, we report a highly regioselective [4 + 2]-annulation of vinyl sulfoxonium ylides with ynoates under light-mediated conditions. The reaction proceeds through the new dienyl ylide, which undergoes photolysis blue light irradiation to give substituted naphthalene scaffolds. method presented here operates at room temperature and does not require addition an external photosensitizer. in situ-generated ylide absorbs acts as photosensitizer for formation arenes. synthetic potential these benzannulations was further illustrated by various transformations scale-up reaction. Moreover, control experiments quantum chemical calculations reveal mechanistic details developed

Language: Английский

Citations

9

Designing radical chemistry by visible light-promoted homolysis DOI
Stefano Protti, Davide Ravelli, Maurizio Fagnoni

et al.

Trends in Chemistry, Journal Year: 2022, Volume and Issue: 4(4), P. 305 - 317

Published: March 1, 2022

Language: Английский

Citations

35

Photoinduced ynamide structural reshuffling and functionalization DOI Creative Commons
Mohana Reddy Mutra, Jeh‐Jeng Wang

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: April 29, 2022

The radical chemistry of ynamides has recently drawn the attention synthetic organic chemists to construction various N-heterocyclic compounds. Nevertheless, ynamide-radical remains a long-standing challenge for due its high reactivity, undesirable byproducts, severe inherent regio- and chemoselective problems. Importantly, ynamide C(sp)-N bond fission an unsolved challenge. In this paper, we observe Photoinduced trigger fission, structural reshuffling functionalization 2-alkynyl-ynamides prepare synthetically inaccessible/challenging chalcogen-substituted indole derivatives with excellent step/atom economy. key breakthroughs work includes, cleavage, divergent precursors, broad scope, easy handle, larger-scale reactions, generation multiple bonds (N-C(sp2), C(sp2)-C(sp2), C(sp2)-SO2R/C-SR, C-I/C-Se/C-H) in few minutes without photocatalysts, metals, oxidants, additives. Control experiments 13C-labeling supporting conclusion that sulfone radicals contribute processes via pathway.

Language: Английский

Citations

33

Spirooxindoles: Recent report of green synthesis approach DOI Creative Commons
Agus Rimus Liandi, Antonius Herry Cahyana,

Diva Naufal Alfariza

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: 5(1), P. 1 - 13

Published: Aug. 15, 2023

Spirooxindole is a compound with unique framework and broad bioactivities in medicine. In this study, we have reviewed various approaches or methods synthesizing spirooxindole derivatives focused on green synthesis. Synthesis of spirooxindoles mainly carried out through multicomponent reactions combined such as the use heterogeneous catalysts (nano-sized, magnetic, metal-complex, metal-organic catalysts), deep eutectic solvent, solvent-free reactions, catalyst-free well ultrasonic microwaves irradiation. The method addition to obtaining high yields, it also offers reductions hazardous chemicals, energy use, purification processes, waste generation. As result, synthesis are more environmentally friendly.

Language: Английский

Citations

21

Visible-Light-Promoted and EDA Complex-Driven [4 + 2] Annulation for the Construction of Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines DOI

Wanting Feng,

Ziren Chen, Fei Xue

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2365 - 2370

Published: March 20, 2024

A green visible-light-promoted and electron donor–acceptor (EDA) complex-driven synthetic strategy for the construction of value-added naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines from 2-arylimidazo[1,2-a]pyridines with Z-α-bromocinnamaldehydes has been accomplished under photocatalyst- transition-metal-free conditions. This efficient annulation approach provides a new straightforward pathway annulative π-extension imidazo[1,2-a]pyridine-based aromatics. Moreover, sustainable methodology exhibits simple operation, wide range substrates, benign conditions, good functional group compatibility.

Language: Английский

Citations

7