Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds

Organic Letters, Год журнала: 2024, Номер 26(12), С. 2511 - 2516

Опубликована: Март 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

Язык: Английский

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Visible-Light-Induced Cascade Cyclization of 1-(2-(Arylethynyl)benzoyl)indoles into Sulfonated Benazepino[1,2-a]indolones

Organic Letters, Год журнала: 2024, Номер 26(50), С. 10982 - 10987

Опубликована: Дек. 10, 2024

1-(2-(Arylethynyl)benzoyl)indoles were developed as an innovative scaffold for radical cascade cyclization under visible-light and mild conditions, enabling efficient synthesis of sulfonated benazepino[1,2-

Язык: Английский

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Photocatalytic selective disulfuration of aryl aldehydes and alkenyl aldehydes with dithiosulfonate as bifunctional disulfur reagent and hydrogen atom accepter

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We developed a photocatalytic method for the selective disulfuration of aryl aldehydes and alkenyl using bifunctional dithiosulfonate (ArSO 2 -SSR), enabling synthesis benzoyl disulfides chroman-4-ones with disulfide moieties.

Язык: Английский

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Nickel-Catalyzed Branched Hydroalkylation of Alkenes with Diazo Compounds

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Фев. 25, 2025

A nickel-catalyzed, branched-selective hydroalkylation of alkenes using diazo compounds has been developed. This protocol enables the functionalization both activated and unactivated alkenes, in directed nondirected manners. Mono-, di-, trisubstituted can be effectively transformed. Highly diastereoselective hydroalkylations have also demonstrated. The method provides a novel approach for introducing an α-carbonyl moiety to which is currently inaccessible by existing methods. Preliminary mechanistic investigations suggest carbene-type mechanism, unusual nickel catalysis.

Язык: Английский

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Photocatalytic Synthesis of Isoquinolinediones via the Cascade Reaction of N-Alkyl-N-methylacrylamides with Diazo Compounds

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 25, 2025

Carbon radicals generated from acceptor diazo compounds prefer to add electron-rich olefins and heteroarenes due their containing electron-withdrawing groups. Herein, a cascade reaction of with electron-deficient is developed. In the presence visible light Ru catalyst, generate carbon via proton-coupled electron transfer process, followed by addition various N-alkyl-N-methylacrylamides subsequent cyclization give series acyl-substituted isoquinolinediones.

Язык: Английский

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Visible-light-driven Synthesis of Benzoxepine Derivatives from Aromatic Diazo Compounds

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134620 - 134620

Опубликована: Март 1, 2025

Язык: Английский

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Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Язык: Английский

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Photoredox‐Catalyzed [3+2] annulation of Aromatic Amides with Olefins via Iminium Intermediates

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Окт. 19, 2024

Despite the preliminary success of transition metal-catalyzed [3+2] annulation amides with olefins, corresponding radical-type remains a laborious challenge. Herein we report first photoredox-catalyzed aromatic olefins. We established an approach to generate unprecedented iminium radicals by reducing oxyiminium intermediates, formed in situ from Tf

Язык: Английский

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Synthesis of β-amino acid derivatives via photoredox-catalyzed radical cross–coupling of anilines with diazo compounds

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(21), С. 6042 - 6047

Опубликована: Янв. 1, 2024

A photoredox-catalyzed radical cross–coupling protocol for the synthesis of β-amino acid derivatives has been developed. This atom-economic enables a range esters in moderate to excellent yields.

Язык: Английский

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Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1H)-ones using water as the hydrogen donor

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110582 - 110582

Опубликована: Ноя. 1, 2024

Язык: Английский

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