Metal-Free Photosynthesis of Alkylated Benzimidazo[2,1-a]isoquinoline-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones in PEG-200

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(13), С. 9055 - 9066

Опубликована: Июнь 23, 2021

A visible-light-induced decarboxylation reaction was developed for the synthesis of alkylated benzimidazo[2,1-a]isoquinoline-6(5H)-ones and indolo[2,1-a]isoquinolin-6(5H)-ones under metal-free conditions. Impressively, metal catalysts traditionally volatile organic solvents could be effectively avoided.

Язык: Английский

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Visible‐Light Photosynthesis of CHF₂/CClF₂/CBrF₂‐Substituted Ring‐fused Quinazolinones in Dimethyl Carbonate

Chemistry - An Asian Journal, Год журнала: 2021, Номер 17(1)

Опубликована: Ноя. 26, 2021

With eco-friendly and sustainable CO2 -derived dimethyl carbonate as the sole solvent, visible-light-induced cascade radical reactions have been established a green efficient tool for constructing various CHF2 /CClF2 /CBrF2 -substituted ring-fused quinazolinones.

Язык: Английский

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Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines

Organic Letters, Год журнала: 2021, Номер 24(1), С. 299 - 303

Опубликована: Дек. 16, 2021

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst can be simply recovered from mixture reused at least five times without an obvious reduction in its reactivity, exhibiting high economic feature.

Язык: Английский

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Visible‐Light‐Curable Acrylic Resins toward UV‐Light‐Blocking Adhesives for Foldable Displays

Advanced Materials, Год журнала: 2022, Номер 35(43)

Опубликована: Июль 28, 2022

Current technological advances in the organic light-emitting diode panel design of foldable smartphones demand advanced adhesives with UV-blocking abilities, beyond their conventional roles bonding objects and relieving deformation stress. However, optically clear (OCAs) ability cannot be prepared using UV-curing methods relying on a photoinitiator. Herein, new acrylic resin that can efficiently cured visible light without oxygen removal is presented, which may used to develop OCAs for use current flexible displays. A novel photocatalyst specific combination additives facilitate sufficiently rapid curing under presence UV-absorbers. Only very small amount highly active required prepare OCA films high transparency region. Using this system, nearly meets specifications an commercialized realized. This technology also utilized other applications require efficient curing, such as resins, dental 3D/4D-printable materials.

Язык: Английский

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Direct benzylation reactions from benzyl halides enabled by transition-metal-free photocatalysis

Chinese Chemical Letters, Год журнала: 2022, Номер 33(12), С. 5074 - 5079

Опубликована: Март 26, 2022

Язык: Английский

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Three-component reaction access to S-alkyl dithiocarbamates under visible-light irradiation conditions in water

Green Chemistry, Год журнала: 2022, Номер 24(3), С. 1302 - 1307

Опубликована: Янв. 1, 2022

An environmentally friendly multicomponent reaction protocol to synthesize S -alkyl dithiocarbamate derivatives from Katritzky salt, CS 2 , and secondary amines under visible light irradiation conditions has been developed.

Язык: Английский

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Cobaloxime Photocatalysis for the Synthesis of Phosphorylated Heteroaromatics

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(40)

Опубликована: Авг. 1, 2022

Abstract Herein, cobaloxime is used for the first time as a catalyst synthesis of phosphorylated heteroaromatics, which an intriguing and versatile functional motif. With visible‐light irradiation, not only oxidizes phosphine oxides to form phosphorus radicals (P‐radicals) subsequent reaction with radical acceptor isocyanides or but also combines intermediate β ‐H elimination, thereby producing heteroaromatics H 2 CH 4 byproduct. Phosphine dialkyl, alkylaryl, diaryl substituents could be directly transformed into phenanthridines, benzothiazoles, isoquinolines, common heteroaromatics. This catalytic system features extremely mild conditions, broad substrate scope good excellent yields. Scale‐up sunlight show great application potential in green important organophosphorus chemicals.

Язык: Английский

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Efficient Aliphatic Hydrogen-Isotope Exchange with Tritium Gas through the Merger of Photoredox and Hydrogenation Catalysts

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(11), С. 5010 - 5022

Опубликована: Март 9, 2022

Employment of a combination an organophotoredox catalyst with Wilkinson's (Rh(PPh3)3Cl) has given rise to unprecedented method for hydrogen-isotope exchange (HIE) aliphatic C(sp3)-H bonds complex pharmaceuticals using T2 gas directly. catalyst, commonly used catalytic hydrogenations, was exploited as precatalyst activation D2 or and hydrogen atom transfer. In this combined methodology mechanistic study, we demonstrate that by coupling photocatalysis Rh catalysis, carbon-centered radicals generated via photoredox catalysis can be intercepted Rh-hydride intermediates deliver effective donor labeling molecules in one step. By optimizing the ratio photocatalyst balance rate dual cycles, achieve efficient HIE high recovery yield. This protocol readily applied direct 10 drug molecules, showing isotope incorporation efficiency exceptionally good functional group tolerance demonstrating approach practical attractive deuteration tritiation.

Язык: Английский

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Visible-Light-Mediated Energy Transfer Enables Cyclopropanes Bearing Contiguous All-Carbon Quaternary Centers

ACS Catalysis, Год журнала: 2023, Номер 13(14), С. 9806 - 9816

Опубликована: Июль 11, 2023

Cyclopropanes bearing contiguous all-carbon quaternary centers continue to attract attention due their bioactivities. However, methods obtain cyclopropanes with remain largely unexplored the high steric hindrance of these compounds. Herein, we report a visible-light-mediated energy-transfer (EnT) strategy realize in situ donor/donor carbenes from readily available N-tosylhydrazones, facilitating synthesis highly congested EWG-free cyclopropanes. Through this approach, are rapidly installed into complex bioactive molecules, fluorescent and other useful building blocks that challenging synthesize. Detailed mechanistic reactions DFT studies clearly demonstrated role photosensitizer, formation carbenes, necessity light base system.

Язык: Английский

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Organophotocatalytic Mechanisms: Simplicity or Naïvety? Diverting Reactive Pathways by Modifications of Catalyst Structure, Redox States and Substrate Preassemblies

ChemCatChem, Год журнала: 2023, Номер 15(11)

Опубликована: Фев. 21, 2023

Abstract Photocatalysis is a powerful tool to assemble diverse chemical scaffolds, yet bottleneck on its further development the understanding of multitude possible pathways when practitioners rely only oversimplified thermodynamic and optical factors. Recently, there growing number studies in field that exploit, inter alia , kinetic parameters organophotocatalysts are synthetically more programmable terms their redox states opportunities for aggregation with target substrate. Non‐covalent interactions play key role enables access new generation reactivities such as those open‐shell organophotocatalysts. In this review, we discuss how targeted structural modifications influence organophotocatalytic mechanisms together underlying principles. We also highlight benefits strategies preassembly static quenching overcome common reactivity issues (e. g., diffusion rate limits energetic limits).

Язык: Английский

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