Challenging Task of Ni-Catalyzed Highly Regio-/Enantioselective Semihydrogenation of Racemic Tetrasubstituted Allenes via a Kinetic Resolution Process

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(11), С. 7419 - 7430

Опубликована: Март 6, 2024

The first earth-abundant transition metal Ni-catalyzed highly regio- and enantioselective semihydrogenation of racemic tetrasubstituted allenes via a kinetic resolution process as challenging task was well established. This protocol furnishes expedient access to diversity structurally important enantioenriched chiral allylic molecules with high regio-, enantio-, Z/E-selectivity. Remarkably, this proceeded one carbon–carbon double bond allenes, which regioselective complementary the Rh-catalyzed asymmetric version. Deuterium labeling experiments density functional theory (DFT) calculations were carried out reveal reasonable reaction mechanism explain regio-/stereoselectivity.

Язык: Английский

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Photoredox-Catalyzed 1,4-Peroxidation–Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes

Organic Letters, Год журнала: 2024, Номер 26(15), С. 2955 - 2959

Опубликована: Апрель 3, 2024

An Eosin Y-catalyzed visible light-promoted 1,4-peroxidation–sulfonylation of enynones was achieved to give tetrasubstituted allenes. The photoredox catalysis Y allowed the concomitant formation peroxy and sulfonyl radicals, where preferential radical addition alkene moiety resulted in subsequent α-keto radical–sulfonyl cross couplings. developed demonstrates a regioselective 1,4-diradical strategy, opening up new possibility diradical functionalization conjugate systems.

Язык: Английский

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Nickel-catalyzed multicomponent 1,4-fluoroalkylcarbonylation of 1,3-enynes to access allenyl ketones

Tetrahedron, Год журнала: 2024, Номер 157, С. 133965 - 133965

Опубликована: Март 28, 2024

Язык: Английский

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Nickel-catalyzed carbonylative four-component 1,4-dicarbofunctionalization of 1,3-enynes

Science China Chemistry, Год журнала: 2024, Номер 67(6), С. 2029 - 2038

Опубликована: Апрель 24, 2024

Язык: Английский

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Visible light promoted synthesis of allenes

Catalysis Science & Technology, Год журнала: 2024, Номер 14(18), С. 5143 - 5160

Опубликована: Янв. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Язык: Английский

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Electrochemical synthesis of allenyl silanes and allenyl boronic esters

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

Опубликована: Май 17, 2025

Allenyl silanes and boronates are pivotal building blocks in organic synthesis. Nevertheless, their synthesis requires the manipulation of transition metal or highly reactive species. Hence, development more sustainable protocol is sought after. Here we show electrochemical allenyl boronic esters. This catalyst-free method proceeds under mild reaction conditions. The for shows an excellent efficiency a good functional group tolerance. isolated yields (28 examples, 45-95% yields) without use catalyst A similar developed boronates, which obtained low to moderate (13 5-55% yields). Finally, mechanism based on oxidative generation silyl boryl radicals suggested access these classes allenes.

Язык: Английский

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Nickel-Catalyzed Reductive 1,4-Alkylacylation of 1,3-Enynes Enabling Synthesis of Allenyl Ketones

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

A nickel-catalyzed reductive 1,4-alkylacylation of 1,3-enynes has been established using nonactivated tertiary alkyl bromides and aromatic anhydrides as dual electrophiles. This protocol enables efficient assembly tetrasubstituted allenyl ketones with high chemo- regioselectivity. Mechanistic insights reveal the radical relay process involving synergistic interactions nickel zinc. The ketone products serve modular building blocks, particularly for constructing fully carbon-substituted furans via Au-catalyzed cycloisomerization selective 1,2-aryl migration, enhancing synthetic practicality.

Язык: Английский

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Rh-Catalyzed Carbonylative Cyclization of Propargylic Alcohols with Aryl Boronic Acids

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6279 - 6283

Опубликована: Июль 18, 2024

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Axially chiral α-boryl-homoallenyl boronic esters as versatile toolbox for accessing centrally and axially chiral molecules

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

Опубликована: Окт. 25, 2024

Язык: Английский

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Divergent reactivity of acrylamides and β-chloroenones under base-controlled palladium catalysis: construction of spirooxindoles and furan-containing 3,3-disubstituted oxindoles

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(2), С. 348 - 357

Опубликована: Ноя. 22, 2023

Divergent synthesis of spirooxindoles and furan-containing oxindoles via base-controlled palladium catalysis was achieved. The key intermediates, allene insertion, Pd–carbene migratory insertion are supported by DFT calculations.

Язык: Английский

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