Nickel-Catalyzed Carbonylative Negishi Cross-Coupling of Unactivated Secondary Alkyl Electrophiles with 1 atm CO Gas

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(12), С. 7971 - 7978

Опубликована: Март 14, 2024

We describe a nickel-catalyzed carbonylative cross-coupling of unactivated secondary alkyl electrophiles with the organozinc reagent at atmospheric CO gas, thus allowing expedient construction unsymmetric dialkyl ketones broad functional group tolerance. The leverage newly developed

Язык: Английский

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Visible‐Light‐Driven Four‐Component Radical Relay Aminocarbonylation of Unactivated Alkenes^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(9), С. 990 - 996

Опубликована: Янв. 18, 2024

Comprehensive Summary Catalytic four‐component radical carbonylation of unactivated alkenes has recently been recognized as a robust protocol for rapid construction various structurally diverse carbonyl compounds. Given the significance fluorine‐containing groups, this reaction class extensively applied to assembly variety perfluoroalkyl carboxylic acid derivatives by transition metal catalysis. Herein, we report visible‐light‐driven relay 1,2‐perfluoroalkylation aminocarbonylation using CO gas source and 4CzIPN organic photocatalyst. A wide range amines were well tolerated, providing valuable β‐perfluoroalkylated amides with generally good yields high chemoselectivity.

Язык: Английский

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Pd‐Catalyzed Synthesis of Aryl Esters Involving Difluorocarbene Transfer Carbonylation

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(10)

Опубликована: Фев. 14, 2024

Abstract A Pd‐catalyzed three‐component intermolecular reaction between aryl halides, ClCF 2 COONa and phenols is developed. series of benzoates were synthesized in up to 84 % yield via difluorocarbene transfer carbonylation. It devoted acquiring the targeted products by construction new C−C, C=O C−O bonds a one‐pot, one‐step process. The feature this method includes use readily available starting materials, showing outstanding resistance spatial obstruction simple operation procedure with mild conditions. Therefore, makes methodology useful alternative other schemes typically used for synthesis esters.

Язык: Английский

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Nickel-Catalyzed Four-Component Carbonylation of 1,3-Butadiene To Access β,γ-Unsaturated Ketones

Organic Letters, Год журнала: 2024, Номер 26(22), С. 4779 - 4783

Опубликована: Май 29, 2024

A new strategy to obtain β,γ-unsaturated ketones via the cross-coupling of 1,3-butadiene, alkyl bromides, and arylboronic acids under 1 bar CO with nickel as catalyst has been developed. This newly developed four-component carbonylation procedure features advantages including using a cheap catalytic system, high step economy, mild reaction conditions, excellent 1,4-regioselectivity, thereby providing sustainable alternative tool for production compared present tactics. To elucidate application potential this method, olefin synthons are derived from representative coupling product.

Язык: Английский

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Nickel-Catalyzed Narasaka–Heck Cyclization Carbonylation of Unsaturated Oxime Esters with Arylboronic Acids

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7834 - 7840

Опубликована: Сен. 5, 2024

The Narasaka-Heck reaction is one of the most straightforward methods for constructing pyrroline derivatives. Herein, we report a novel nickel-catalyzed three-component carbonylation reaction, which cleverly realizes continuous construction C(sp

Язык: Английский

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Nickel-catalyzed acylation of vinylpyridine with alkylzincs under 1 atm CO

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2380 - 2383

Опубликована: Янв. 1, 2024

A nickel-catalyzed acylation of vinylpyridines with CO at atmospheric pressure is reported, allowing for an expedient approach to synthesize β-acyl pyridine derivatives high regio- and chemoselectivity. The electron-withdrawing property plays pivotal roles in activating the alkenyl group, thereby facilitating this carbonylative process. In addition vinylpyridines, other alkenylheterocycles such as thiazole quinoline were also suitable method.

Язык: Английский

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Photoredox-catalyzed carbonylative acylation of styrenes with Hantzsch esters

Chemical Communications, Год журнала: 2024, Номер 60(35), С. 4656 - 4658

Опубликована: Янв. 1, 2024

A three-component carbonylation that provides a new method for the synthesis of ketones from Hantzsch esters has been developed.

Язык: Английский

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Nickel Catalyzed Carbonylative Cross Coupling for Direct Access to Isotopically Labeled Alkyl Aryl Ketones

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(51)

Опубликована: Авг. 15, 2024

Here we present an effective nickel-catalyzed carbonylative cross-coupling for direct access to alkyl aryl ketones from readily accessible redox-activated tetrachlorophthalimide esters and boronic acids. The methodology, which is run employing only 2.5 equivalents of CO simple Ni(II) salts as the metal source, exhibits a broad substrate scope under mild conditions. Furthermore, this carbonylation chemistry provides easy switch between isotopologues stable (

Язык: Английский

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Palladium-catalyzed difluorocarbene transfer enables access to enantioenriched chiral spirooxindoles

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Окт. 1, 2024

Язык: Английский

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P^III/P^V═O Redox Catalysis Mediated Thioesterification of Carboxylic Acids with Disulfides under Air Conditions

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

Опубликована: Янв. 12, 2025

An efficient organophosphorus-catalyzed thiocarbonylation reaction of disulfides with carboxylic acids under air conditions was described. Various functional groups on and can be tolerated the present conditions, affording thioesters in good to excellent yields. This method exhibited chemoselectivity applied for late-stage functionalization drug molecules containing a acid group.

Язык: Английский

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