Photoredox/nickel dual-catalyzed deaminative cross-electrophile for allenylic alkylation with non-activated alkyl katritzky salts

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5685 - 5694

Опубликована: Янв. 1, 2024

The first allenylic alkylation with non-activated aliphatic amine derivatives, Katritzky salts, has been developed via photoredox/nickel dual-catalyzed reductive deaminative cross-electrophile coupling.

Язык: Английский

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Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh₃ Catalysis

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 10, 2024

Comprehensive Summary A visible‐light‐induced decarboxylative radical cascade cyclization reaction between N ‐(2‐cyanoaryl)‐acrylamides and alkyl ‐(acyloxy)phthalimide (NHPI esters) for the construction of phenanthridine derivatives has been developed. This approach utilizes lithium iodide (LiI) triphenylphosphine (PPh 3 ) as redox catalysts is produced through photoactivation electron donor‐acceptor (EDA) complex. series primary, secondary, tertiary alkyl‐substituted phenanthridines are prepared in up to 82% yield without transition‐metal catalysts, chemical oxidants, or metal‐/organic dye‐based photocatalysts.

Язык: Английский

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Nickel‐Catalyzed Electrochemical Cross‐Electrophile C(sp²)−C(sp³) Coupling via a Ni^II Aryl Amido Intermediate

Angewandte Chemie, Год журнала: 2024, Номер 136(38)

Опубликована: Июнь 8, 2024

Abstract Cross‐electrophile coupling (XEC) between aryl halides and alkyl is a streamlined approach for C(sp 2 )−C(sp 3 ) bond construction, which highly valuable in medicinal chemistry. Based on key Ni II amido intermediate, we developed selective scalable Ni‐catalyzed electrochemical XEC reaction (hetero)aryl primary secondary halides. Experimental computational mechanistic studies indicate that an amine ligand slows down the oxidative addition process of Ni‐polypyridine catalyst to bromide intermediate formed situ during process. The relatively slow beneficial enhancing selectivity reaction. stabilizes –aryl species prevent aryl–aryl homo‐coupling side reactions acts as activate substrates. This electrosynthesis system provides facile, practical, platform formation (hetero)aryl–alkyl bonds using standard catalysts under mild conditions. insights from this work could serve great foundation future cross‐couplings.

Язык: Английский

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Synthesis of Secondary Boronates via Deaminative Cross‐Coupling of Alkyl Nitroso Carbamates and Boronic Acids

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(37)

Опубликована: Авг. 2, 2024

Abstract A strategy for transition metal‐free cross‐coupling of alkyl nitroso‐carbamates and boronic acids is reported. The N ‐nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows synthesis a wide variety secondary boronates, benzylic boronates formal Csp 3 −Csp 2 products under operationally conditions. Functional group tolerance also demonstrated applied modification lysine to make non‐canonical amino acids.

Язык: Английский

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Synthesis and reactivity of isomeric Ru complexes with hydroxypyridyl fragment: active catalysts for β‑alkylation of secondary alcohols with primary alcohols

Journal of Molecular Structure, Год журнала: 2024, Номер 1321, С. 140159 - 140159

Опубликована: Сен. 23, 2024

Язык: Английский

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