Electroreductive deuteroarylation of alkenes enabled by an organo-mediator

Chemical Science, Год журнала: 2024, Номер 15(29), С. 11418 - 11427

Опубликована: Янв. 1, 2024

An environmentally friendly electroreduction approach is disclosed for site-specific introduction of deuterium via anti-Markovnikov selective deuteroarylation alkenes and aryl iodides with bipyridine as a mediator D 2 O ‘D’ source.

Язык: Английский

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Palladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines

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

Опубликована: Янв. 9, 2025

The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety poly substituted pyridines. protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by cyclization enaminone intermediates with β-ketonitriles enolates, respectively, does not require extra ammonias. This method boasts notable advantages, such as the use commercially available easily prepared substrates, simple conditions, broad substrate scope, good functional group tolerance.

Язык: Английский

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Construction of Amidines via palladium-catalyzed three-component reaction of Arylacetylenes, t-Butylisonitrile and O-benzoyl Hydroxylamines

Tetrahedron Letters, Год журнала: 2025, Номер unknown, С. 155534 - 155534

Опубликована: Март 1, 2025

Язык: Английский

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Electrochemical Synthesis of Vinyl Sulfonates Mediated by Bromine Radicals

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

Vinyl sulfonates are vital intermediates in organic synthesis, serving as versatile electrophiles various cross-coupling reactions. Despite their significance, direct methods for synthesizing vinyl from styrenes have been limited. In this study, we introduce an innovative electrochemical approach that leverages bromine radical mediation to facilitate the synthesis of sulfonates, cheap nBu4NBr acts both electrolyte and a catalytic amount. This process involves reaction with sodium sulfinates water under conditions, offering straightforward pathway these compounds. The developed strategy is characterized by its high efficiency, operational simplicity, environmentally benign nature, adhering principles green chemistry while ensuring atom economy remarkable regioselectivity. Furthermore, methodology proves effective gram-scale allows subsequent functionalization sulfonate products pharmaceutical derivatives, thus broadening potential applications techniques styrene functionalization.

Язык: Английский

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Electrochemically Promoted Synthesis of N-Sulfonyl Sulfinimidate Esters and Sulfilimines from Sulfonamides, Thiophenols, Thioethers, and Alcohols

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

Опубликована: Май 9, 2025

In this work, we report an electrochemical method for the straightforward preparation of scarcely accessible sulfinimidate esters from readily available sulfonamides, thiophenols, and alcohols. Mechanistic experiments show that sulfur oxidation at anodic surface generates electrophilic intermediate, which subsequently undergoes nucleophilic substitution. Moreover, sulfilimines can be obtained in moderate-to-excellent yields when thioethers are used as S-donor instead thiophenols via a dehydrogenateive imination process. This is also characterized by mild reaction condition, operational simplicity, high atomic economic efficiency, easy later drug synthesis, modification, well scaling up to gram scale.

Язык: Английский

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Access to amidines via C(sp²)–N coupling of trifluoroborate-iminiums with N-fluorobenzenesulfonimide

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Amidines are an important class of organic compounds with widespread application as superbases, nucleophilic catalysts, and building blocks heterocyclic in synthesis. Moreover, they represent structural motif medicinal chemistry. This work describes primary trifluoroborate-iminiums unprecedented azide- transition-metal-free transformation to N-sulfonyl amidines the presence N-fluorobenzenesulfonimide (NFSI). novel C(sp2)-N bond-forming reaction proceeds without excess any reagent, under mild conditions provides good high yields by a simple isolation procedure. Density functional theory (DFT) mechanistic studies into this support that use base is required activate either trifluoroborate-iminium or NFSI promote bond formation via attack nitrogen. The utility developed methodology showcased synthesis two bioactive compounds.

Язык: Английский

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Manganaelectro-Catalyzed Cyclization of o-Aminoarylketones with Ammonia: An Approach to 1,2-Dihydroquinazolines

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 12, 2024

A manganaelectro-catalyzed cyclization reaction of 2-aminoarylketones with simple alcohols and ammonia under mild conditions is reported for the first time. The cooperative catalysis effectively enhances oxidation primary into aldehydes, thus enabling synthesis substituted 1,2-dihydroquinazolines in good to excellent yields. In addition, utilities this method are highlighted construction biologically active molecules that would otherwise be difficult access through a traditional method.

Язык: Английский

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Direct N H heteroarylation of NH-sulfoximines under electrochemical conditions

Molecular Catalysis, Год журнала: 2024, Номер 568, С. 114485 - 114485

Опубликована: Авг. 27, 2024

Язык: Английский

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Electrochemical Selenocyclization of N-Alkyl anilines: Access to 3-Selenyl quinolines

Tetrahedron, Год журнала: 2024, Номер unknown, С. 134257 - 134257

Опубликована: Сен. 1, 2024

Язык: Английский

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One-pot Synthesis of N-Sulfonylamidines from N-Acylsulfonamides Enabled by a Metal Triflate-Mediated Nonhydrolytic N-Deacylation†

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

A one-pot method has been developed to prepare N -sulfonylamidines from -acylsulfonamides via a metal triflate-catalyzed nonhydrolytic deacylation followed by interception of the newly formed sulfonamide with , -dimethylformamide dimethyl acetal.

Язык: Английский

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