Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Янв. 24, 2025

C–C bond cleavage and recombination provide an efficient strategy for the modification reconstruction of molecule structures. Herein, we present a method achieving amidation aryl C(sp2)–H through triple with involvement nitrous acid esters. This marks instance precise controlled stepwise bond, offering fresh perspective such bonds. Nitrous ester serves as both radical source hydrogen atom transfer (HAT) reagent to functionalize utilize two carbon atoms bond. The alkoxy captures from or N-hydroxyl induce 1,3-oxygen migration, which is crucial subsequent molecular authors report achieve bonds by participation

Язык: Английский

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Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(8), С. 2195 - 2200

Опубликована: Янв. 1, 2024

A Heck-like coupling of cyclic sulfonium salts with alkenes via selective C–S bond cleavage using a copper complex as photosensitizer through visible-light-driven redox-neutral process has been developed.

Язык: Английский

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Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis

Organic Letters, Год журнала: 2023, Номер 25(30), С. 5563 - 5568

Опубликована: Июль 21, 2023

A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF3 functional groups. Remarkably, incorporation NH2 group onto 1,3-enyne moiety enabled further cyclization give unique scaffold containing lactone an indole moiety.

Язык: Английский

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Efficient Low-Temperature catalytic depolymerization of LLDPE into valuable compounds using H-ZSM-5 catalysts and water

Fuel, Год журнала: 2024, Номер 366, С. 131356 - 131356

Опубликована: Март 2, 2024

Язык: Английский

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Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds

Organic Letters, Год журнала: 2024, Номер 26(34), С. 7170 - 7175

Опубликована: Авг. 19, 2024

A cascade reaction of cyclopropyl alcohols, DABSO (1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate), and N-(sulfonyl)acrylamides has been developed. This tandem process went through a cyclopropanol ring opening Michael addition sequence. The γ-keto sulfinate generated from the between serves as nucleophilic reagent, N-(sulfonyl)acrylamide is used acceptor. By utilizing this strategy, multitudinous sulfone-bridged 1,7-dicarbonyl compounds that contain both β-sulfonyl amide unit sulfone skeleton were conveniently synthesized.

Язык: Английский

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Visible-Light-Promoted C(sp³)–C(sp³) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination

Organic Letters, Год журнала: 2023, Номер 25(48), С. 8733 - 8738

Опубликована: Ноя. 22, 2023

A photoredox-catalyzed approach for the difluoroalkylation of amino acids was achieved through simultaneous decarboxylation and defluorination processes. This innovative protocol employs commonly available trifluoroacetophenones as primary starting materials, eliminating necessity preactivation. strategy has enabled synthesis several difluoroketone functionalized amines in moderate to impressive yields. These synthesized compounds are presented foundational molecules subsequent modification. The underlying mechanism transformation is anchored a single electron transfer (SET) radical pathway.

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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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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Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 28, 2024

Язык: Английский

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