A new approach for the copper-catalyzed functionalization of alkyl hydroperoxides with organosilicon compounds via in-situ-generated alkylsilyl peroxides

Tetrahedron, Год журнала: 2022, Номер 112, С. 132627 - 132627

Опубликована: Янв. 8, 2022

Язык: Английский

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Fe-Catalyzed Dicarbofunctionalization of Vinylarenes with Alkylsilyl Peroxides and β-Keto Carbonyl Substrates

Organic Letters, Год журнала: 2022, Номер 24(14), С. 2641 - 2645

Опубликована: Март 4, 2022

The formation of two carbon-carbon bonds using vinylarenes with alkylsilyl peroxides and β-keto carbonyl substrates is effected by the presence catalytic Fe(OTf)2 under mild reaction conditions. A variety different substituents can be utilized in combination several substrates.

Язык: Английский

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Nickel-Catalyzed Radical Ring-Opening Phosphorylation of Cycloalkyl Hydroperoxides Leading to Distal Acylphosphine Oxides

Organic Letters, Год журнала: 2023, Номер 25(6), С. 928 - 932

Опубликована: Фев. 2, 2023

A facile and efficient nickel-catalyzed C-C bond cleavage/phosphorylation of various cycloalkyl hydroperoxides was developed. This radical ring-opening strategy provided practical access to structurally diverse distal ketophosphine oxides in one pot through concurrent C═O/C-P formation with high atom economy under mild room temperature base-free conditions.

Язык: Английский

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Copper‐Catalyzed Asymmetric Radical 1,2‐Alkylesterification of 1,3‐Dienes with Cycloalkyl Hydroperoxides and Acids

ChemCatChem, Год журнала: 2023, Номер 15(23)

Опубликована: Окт. 17, 2023

Abstract Transition‐metal‐catalyzed radical relay cross‐coupling reactions of 1,3‐dienes have recently emerged as one the most powerful methods for construction structurally diverse allylic compound in a single chemical step. However, there still has been limited success expanding substrate scope precursors and coupling partners, well exploring catalytic asymmetric variants. Herein, we report copper‐catalyzed enantioselective three‐component 1,2‐alkylesterification using cycloalkyl hydroperoxides carbonyl‐containing alkyl sources carboxylic acids O‐nucleophiles under mild redox‐neutral conditions. This protocol features broad good functional group tolerance with respect to each component, providing practical access variety distally keto‐functionalized esters high enantioselectivity. Mechanistic studies suggest involvement sequential C−O this reaction.

Язык: Английский

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Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2370 - 2374

Опубликована: Янв. 1, 2024

An efficient method was developed for the one-pot construction of pyrrolo[1,2- a ]quinoxalines via Cu( ii )-catalyzed domino reaction between 2-(1 H -pyrrol-1-yl)anilines and alkylsilyl peroxides.

Язык: Английский

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Photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade

Chemical Communications, Год журнала: 2024, Номер 60(40), С. 5334 - 5337

Опубликована: Янв. 1, 2024

A photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade is developed. The protocol features broad substrate scope and excellent functional group compatibility.

Язык: Английский

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Copper-catalyzed redox neutral ketoalkylation of Csp²–H bonds via C–C bond cleavage

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(20), С. 5866 - 5871

Опубликована: Янв. 1, 2021

An efficient copper-catalyzed ketoalkylation of Csp 2 –H bonds with cycloalkyl silyl peroxides under mild conditions is presented. A series in quinoxalin-2(1 H )-ones, heteroaromatic N -oxides and quinones were amenable to this protocol.

Язык: Английский

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Organophotoredox-catalyzed ring-opening gem-difluoroallylation of nonstrained cycloalkanols

Molecular Catalysis, Год журнала: 2022, Номер 533, С. 112788 - 112788

Опубликована: Ноя. 4, 2022

Язык: Английский

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p-Methoxybenzyl-Radical-Promoted Chemoselective Protection of sec-Alkylamides

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2575 - 2582

Опубликована: Фев. 2, 2023

The hitherto difficult site-selective p-methoxybenzylation of secondary amides using p-methoxybenzylated alkylsilyl peroxides as a novel agent under copper catalysis is reported. reaction proceeds mild conditions in highly chemoselective manner. This approach was successfully applied to the peptides.

Язык: Английский

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Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C–C Bond Cleavage/Cyclization of N-Functionalized Acrylamides

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 9927 - 9940

Опубликована: Июль 11, 2023

An array of redox-neutral alkylation/cyclization cascade reactions N-functionalized acrylamides with cycloalkyl hydroperoxides were achieved via the alkoxyl radical-triggered C-C bond cleavage. Through adjusting radical acceptors on N atom, a variety keto-alkylated chain-containing azaheterocycles, including indolo[2,1-a]isoquinolin-6(5H)-ones, quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridines constructed by one-pot procedure good yields excellent functional group tolerance.

Язык: Английский

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