TEMPO Mediated Cyclopropanols Ring Opening C−N Cross‐Coupling with Nitrogen Nucleophiles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(10), С. 1678 - 1684

Опубликована: Апрель 28, 2023

Abstract A feasible and umpolung strategy for the synthesis of structurally diverse β ‐amino ketones has been achieved through TEMPO mediated C−N coupling cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from are key intermediates play multiple roles, including radical initiator, trapping reagent, a porter ‐hydrogen an base. This protocol features broad substrate scope, good scalability to excellent yields provides alternative complementary approach important ketone scaffolds under metal additive‐free conditions. magnified image

Язык: Английский

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Amidative β-Scission of Alcohols Enabled by Dual Catalysis of Photoredox Proton-Coupled Electron Transfer and Inner-Sphere Ni-Nitrenoid Transfer

Journal of the American Chemical Society, Год журнала: 2023, Номер 146(1), С. 1001 - 1008

Опубликована: Дек. 18, 2023

The photoredox/Ni dual catalysis is an appealing strategy to enable unconventional C-heteroatom bond formation. While significant advances have been achieved using this system, intermolecular C(sp

Язык: Английский

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Copper-catalyzed synthesis of primary amides through reductive N–O cleavage of dioxazolones

RSC Advances, Год журнала: 2024, Номер 14(14), С. 9440 - 9444

Опубликована: Янв. 1, 2024

A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. broad scope exhibited as well containing biologically active structural motifs. These robust and conditions allow transformation to amides, sensitive functional groups such hydroxyl, aldehyde, trialkylsilyl, unsaturated carbon units tolerated excellent chemoselectivity.

Язык: Английский

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Fluoride-promoted Ni-catalyzed cyanation of C-O bond using CO2 and NH3

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110206 - 110206

Опубликована: Июль 1, 2024

Язык: Английский

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Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 200 - 216

Опубликована: Янв. 22, 2025

Over the past decade, dioxazolones have been widely used as N -acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among 3d metals, copper catalysts gaining increasing attention owing to their abundance, cost-effectiveness, sustainability. Recently, applied chemical transformation dioxazolones, conferring a convenient protocol towards amidated products. This review highlights recent advancements synthetic transformations particular examples salts.

Язык: Английский

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Photo‐Promoted Nitrogen‐Centered Radical Mediated Intermolecular Aminative Carbonylation of Tertiary Allyl Alcohols to Access β‐Amino Ketones through (Hetero)Aryl Migration

ChemistryEurope, Год журнала: 2025, Номер unknown

Опубликована: Март 12, 2025

Abstract Carbon monoxide, as a crucial C1 synthon, has been widely used in the difunctionalization of alkenes. Additionally, nitrogen‐centered radicals (NCRs) are also effective intermediates for constructing C−N bonds. Herein, radical‐mediated aminative carbonylation strategy producing β ‐amino ketones from tertiary allyl alcohols disclosed. Good yields with different functional groups were generated effectively under light irradiation.

Язык: Английский

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Rh-Catalyzed Coupling of Cyclic 1,3-Dicarbonyl-Derived Iodonium Ylides with Cyclopropanols

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

Herein, we report a modular α-monoalkylation of cyclic 1,3-dicarbonyls with cyclopropyl alcohols through iodonium ylide strategy. This approach is general, base-free, operationally simple, and suitable for various medically important (hetero)cyclic 1,3-dicarbonyls. A wide range alcohols, easily prepared from feedstock chemicals, can serve as complement alkylating agents. Importantly, the newly formed carbonyl groups in resulting products provide versatile platform numerous synthetic applications.

Язык: Английский

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Iron-Catalyzed Three-Component Reactions of Cyclopropanols with Alkenes and N-Heteroarenes via Ring-Opening and C–H Functionalization

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 13, 2025

An iron-catalyzed ring-opening multicomponent reaction of cyclopropyl alcohols with alkenes and N-heteroarenes involving aryl C(sp2)-H functionalization was developed. This protocol facilitates the regioselective introduction both β-carbonyl moiety an N-heteroarene group across C═C bond alkene, thus allowing a straightforward, efficient, facile access to 5-heteroarene ketones. In this process, strategy relies on alkyl radical formation from alcohols, addition bonds, heteroaryl cascades. general approach displays excellent selectivity control broad functional-group tolerance.

Язык: Английский

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Reaction of Dioxazolones with Boronic Acids: Copper-Mediated Synthesis of N-Aryl Amides via N-Acyl Nitrenes

Organic Letters, Год журнала: 2022, Номер 24(27), С. 4925 - 4929

Опубликована: Июль 1, 2022

Dioxazolones, as direct amide sources, have been used with boronic acids in the presence of copper(I) chloride to access N-aryl amides at room temperature. The versatility developed reaction is proven by ample scope having a wide range functional group tolerance. optimization conditions revealed that fluorine additive demonstrated improved reactivity toward intended transformation. addition triphenylphosphine resulted N-acyl iminophosphorane, suggesting involvement an nitrene intermediate.

Язык: Английский

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Application of Ligands in Cp*Rh(III)-Catalyzed C—H Bond Functionalization Reaction

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(3), С. 924 - 924

Опубликована: Янв. 1, 2023

配体在 Cp*Rh(III

Язык: Английский

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