Recent Advances toward Electro- and Electrophotochemical 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Catalyzed C—H/C—F Bonds Functionalization

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 668 - 668

Опубликована: Янв. 1, 2025

Язык: Английский

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Application of Lead-Free Metal Halide Perovskite Heterojunctions for the Carbohalogenation of C–C Multiple Bonds

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

A graphitic carbon nitride/lead-free double perovskite heterojunction (g-C3N4/Cs2AgBiCl6) has been adopted as a heterogeneous photocatalyst under visible light irradiation. The employed material enabled the atom transfer radical addition-type carbohalogenation of multiple C-C bonds, including (internal) alkenes and alkynes, with alkyl halides. protocol showed remarkable functional group tolerance, compatible late-stage functionalization natural pharmaceutical derivatives, could be easily scaled up, delivering >1 g desired products.

Язык: Английский

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Mild Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

Here we report the use of a tetrabutylammonium decatungstate (TBADT)/thiol photocatalytic system for selective addition acetone and other simple ketone, nitrile, chlorocarbon functionalities to terminal olefins. This avoids energetic reagents such as peroxides proceeds under mild conditions using Earth-abundant element catalysts, providing sustainable approach C-C bond formation activated Initial exploration reveals that hydroalkylation unactivated olefins is also possible, though in lower efficiency, preliminary mechanistic experiments are consistent with radical mechanism.

Язык: Английский

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Electrochemical Reduction of Benzo[b]thiophene 1,1‐Dioxides with HFIP as Hydrogen Donor^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 42(6), С. 585 - 591

Опубликована: Ноя. 2, 2023

Comprehensive Summary A straightforward electrochemical reduction of benzo[ b ]thiophene 1,1‐dioxides with HFIP as the hydrogen donor has been reported in an undivided cell under metal‐free conditions. Moreover, tolerance various functional groups and scaled‐up experiments showed practicability potential applications this methodology.

Язык: Английский

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Electrophotoredox cerium-catalyzed decarboxylative radical cyclization cascade for the synthesis of alkylated benzimidazo-fused isoquinolinones

Catalysis Science & Technology, Год журнала: 2024, Номер 14(4), С. 1037 - 1042

Опубликована: Янв. 1, 2024

We report an electrophotoredox cerium-catalyzed LMCT strategy to incorporate carboxylic acids into radical cyclization cascades. This protocol provides a solution address the challenges in alkylated benzimidazo-fused isoquinolinone synthesis.

Язык: Английский

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Selective Hydro‐ and Deuterodechlorination of Trichloroacetamides under Controlled Electrochemical Conditions To Prepare Mono‐, Di‐, and Deuterochloroacetamides

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2696 - 2704

Опубликована: Апрель 27, 2024

Abstract Mono‐ and dichloro acetamides were prepared via a hydrodechlorination reaction of trichloroacetamides under controlled electrochemical conditions. The reactions carried out in an undivided cell with constant current flow using n ‐Bu 4 NI as supporting electrolyte methanol solvent proton source. Deuterodechlorination trichloroacetamide was also successful when methanol‐ d used identical

Язык: Английский

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Polychloromethylation‐Initiated Radical 1,2‐Aryl Migration of α,α‐Diarylallyl Alcohols via Visible‐Light Photoredox Catalysis

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(31)

Опубликована: Июнь 15, 2023

Abstract A visible‐light induced radical 1,2‐aryl migration of α,α‐diarylallyl alcohols was developed under mild and metal‐free conditions. Commercially available CHCl 3 CH 2 Cl were used as tri‐ dichloromethyl precursors. Structurally diverse β‐polochloromethylated ketones obtained in good to moderate yields via neophyl‐type rearrangement. Besides, the polychloromethyl group can be easily transformed into other useful functional groups.

Язык: Английский

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Electrochemical Oxidative Ring‐Opening Reactions of 2H‐Indazoles with Alcohols to Obtain Ortho‐alkoxycarbonylated Azobenzenes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(9), С. 2020 - 2025

Опубликована: Март 18, 2024

Abstract A strategy for synthesis of azo‐derived compounds by electrochemical oxidative ring‐opening reactions 2 H ‐indazoles with alcohols is reported. The are carried out under galvanostatic electrolysis conditions in an undivided cell without the use transition metal catalysts. On basis cyclic voltammetry and control experiments, a plausible mechanism this reaction involving radical pathway proposed. Furthermore, various suitable system, giving desired ortho‐alkoxycarbonylated azobenzenes 9–84% yields.

Язык: Английский

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Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions

Synthesis, Год журнала: 2023, Номер 55(18), С. 3026 - 3032

Опубликована: Авг. 2, 2023

Abstract An electrochemical approach for the Minisci-type acylation of quinoxalines with α-keto acids as acyl radical precursors is reported. With assistance TFA key additive, acylated were constructed in synthetically useful yields. The distinguishable features this protocol include catalyst- and external oxidant-free conditions, operational simplicity.

Язык: Английский

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Direct alkylation of quinoxalinones with electron-deficient alkenes enabled by a sequential paired electrolysis

Chemical Communications, Год журнала: 2023, Номер 59(85), С. 12763 - 12766

Опубликована: Янв. 1, 2023

The metal-free alkylation of N-heterocycles with alkenes has remained a synthetic challenge. We report here the successful implementation quinoxalinones electron-deficient enabled by sequential paired electrolysis. This protocol provides mechanistically distinct approach to prepare variety C-3 alkylated that are otherwise quite difficult synthesize other means.

Язык: Английский

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