Ferrocene-Mediated Photocatalytic Annulation of N-Sulfonyl Ketimines on a Polycrystalline WSe₂ Semiconductor Photocatalyst

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 13071 - 13076

Published: Sept. 22, 2023

A merger of heterogeneous polycrystalline WSe2 semiconductor photocatalysis and homogeneous ferrocene redox catalysis for the cascade radical coupling-annulation reactions was established. In redox-mediated photocatalysis, can improve separation photogenerated hole–electron pairs on by consuming hole via formation a cation, which triggered molecular transformations. Various benzo[e]imidazo[1,5-c][1,2,3]oxathiazine 5,5-dioxides were formed through semiheterogeneous three-component reaction N-sulfonyl ketimines, N-arylglycines, formaldehyde.

Language: Английский

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Photoinduced, additive- and photosensitizer-free multi-component synthesis of naphthoselenazol-2-amines with air in water

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7983 - 7987

Published: Jan. 1, 2023

An atom- and step-economical, efficient eco-friendly method for constructing naphthoselenazol-2-amines through a visible-light photocatalytic multi-component reaction under aqueous phase conditions is reported.

Language: Английский

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External photocatalyst-free C-H alkylation of N-sulfonyl ketimines with alkanes under visible light

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(9), P. 108509 - 108509

Published: April 28, 2023

Language: Английский

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EtOH-catalyzed electrosynthesis of imidazolidine-fused sulfamidates fromN-sulfonyl ketimines,N-arylglycines and formaldehyde

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(14), P. 5539 - 5542

Published: Jan. 1, 2023

With formaldehyde as an atom-economical carbonyl synthon, the EtOH-catalyzed electrochemical multicomponent synthesis of various imidazolidine-fused sulfamidates under organic oxidant-free, energy-saving and mild conditions was developed.

Language: Английский

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

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

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Synthesis of 1-(Halo)alkyl-3-heteroaryl Bicyclo[1.1.1]pentanes Enabled by a Photocatalytic Minisci-type Multicomponent Reaction

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(8), P. 6247 - 6258

Published: April 10, 2024

Aryl-substituted bicyclo[1.1.1]pentane (BCP-aryl) derivatives represent the most important bioisosteres of biaryl scaffolds and widely exist in numerous complex pharmaceutical molecules. The current synthetic method limitations using only tertiary radical precursors, prefunctionalized heteroarenes, toxic transition metals, expensive photocatalysts make it urgent to develop a more simple practical protocol. To confront enrich Minisci-type chemistry, herein, we disclose photocatalytic multicomponent reaction for synthesis various (halo)alkyl BCP-aryls [1.1.1]propellane, alkyl halides, unfunctionalized heteroarenes as starting materials. Diverse kinds radicals (primary, secondary, carbons) derived from chlorides, bromides, fluoroalkyl iodides are very compatible this transformation. practicability is additionally boosted by product derivatizations late-stage functionalization pharmaceutically relevant mechanistic studies demonstrate that relay mechanism initiated consecutive photoinduced electron transfer (ConPET) process operation. We anticipate methodology would act useful tool biaryl-type drug derivatives, ultimately resulting great utility discovery program.

Language: Английский

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Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110112 - 110112

Published: June 25, 2024

Language: Английский

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Paired Electrolysis-Enabled Arylation of Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(9), P. 6117 - 6125

Published: April 24, 2024

The first paired electrolysis-enabled arylation of quinoxalin-2(1H)-ones was achieved using cyanoarenes as the reagents. A variety 3-arylquinoxalin-2(1H)-ones with various important functional groups were obtained in moderate to good yields under metal- and chemical oxidant-free conditions. With a pair reductive oxidative processes occurring among substrates reaction intermediates, power consumption can be dramatically reduced.

Language: Английский

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Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp³)–H Pyridination of Carbonyls

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

In this study, a novel approach that combines photoinduced electron transfer (ET) with hydrogen atom (HAT) has been introduced for the selective β-C(sp3)–H pyridination of carbonyl compounds. This method is notable its absence transition metals and ability to function under benign reaction conditions, resulting in range pyridinated derivatives consistently moderate good yields. The significance technique further underscored by potential late-stage functionalization pharmaceutically significant molecules. Mechanistic investigations confirmed proceeds via radical-mediated pathway.

Language: Английский

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Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions

Organic Letters, Journal Year: 2025, Volume and Issue: 27(10), P. 2526 - 2531

Published: March 5, 2025

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature our study is ability to perform both using different types The reaction system highly compatible a range aldehydes, yielding C3-esterified C3-alkylated products in moderate-to-good yields. applicability this approach further enhanced by its scalability through continuous-flow synthesis, late-stage modification significant molecules, product derivatization. Our mechanistic investigations reveal radical relay mechanism, triggered hydrogen atom transfer process.

Language: Английский

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