Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis

Chemical Reviews, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 26, 2024

Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp

Язык: Английский

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Nickel-Catalyzed Reductive Alkylation of Pyridines via C–N Bond Activation

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 15, 2025

In this work, we utilized 2-pyridylpyridones as substrates for a reductive transformation with alkyl bromides via C-N bond activation through Ni-catalyzed cross-electrophile coupling platform to efficiently construct 2-alkylpyridines at room temperature. The reaction allowed the use of variety sensitive electronic substituents on both agents. Yields up 95% can be achieved using wide array pyridylpyridones pyridyl precursors. addition, applications in late-stage functionalization natural products and drugs enhanced its potential.

Язык: Английский

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Visible-Light-Induced C–F and C–N Bond Cleavage for the Synthesis of gem-Difluoroalkenes

Organic Letters, Год журнала: 2022, Номер 24(36), С. 6566 - 6570

Опубликована: Сен. 2, 2022

Herein, we describe a novel and efficient photoredox catalytic radical addition/defluoroalkylation coupling reaction between primary amines trifluoromethyl-substituted alkenes. A series of gem-difluoroalkenes were synthesized via C–N bond cleavage α-3°, α-2°, α-1° under visible light irradiation. This is characterized by broad substrate scope good functional group tolerance.

Язык: Английский

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Palladium-catalyzed Heck cyclization/carbonylation with formates: synthesis of azaindoline-3-acetates and furoazaindolines

Chemical Communications, Год журнала: 2022, Номер 58(48), С. 6825 - 6828

Опубликована: Янв. 1, 2022

We report herein a palladium-catalyzed domino cyclization/carbonylation to access ester-functionalized azaindolines, applying formates as convenient carbonyl source. All four azaindoline isomers were constructed, exhibiting good functional group compatibility. On this basis, modifying the starting tether on aminopyridine led furoazaindolines via an intramolecular reductive cyclization after process.

Язык: Английский

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Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction

Organic Letters, Год журнала: 2022, Номер 24(32), С. 6093 - 6098

Опубликована: Авг. 4, 2022

A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been established. This method enables the synthesis of 3,5-vicinal carbocyclic rings found in numerous biologically active compounds and natural products. We provide mechanistic experiments that indicate this proceeds through alkyl iodides formed situ, initiates at secondary electrophilic center, radical intermediates.

Язык: Английский

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Enantioselective reductive aryl-benzylation of alkenes by a nickel-titanium bimetallic system

Cell Reports Physical Science, Год журнала: 2023, Номер 4(7), С. 101474 - 101474

Опубликована: Июнь 27, 2023

The direct use of alcohols as coupling partners via homolytic C–OH bond cleavage remains a formidable challenge but holds great opportunities to achieve useful transformations. In this context, the free precursors carbon radicals in nickel-catalyzed asymmetric dicarbofunctionalization tethered olefins is highly desirable. Reported herein an reductive aryl-benzylation alkenes using benzyl mediated by nickel-titanium bimetallic system. reaction affords corresponding chiral benzene-fused cyclic compounds including oxindoles, dihydrobenzofurans, tetralins, indane, and isochroman bearing all-carbon quaternary stereocenter with up 99% enantiomeric excess. practical utilities protocol are demonstrated late-stage modification some scaffolds pharmaceuticals natural products. This study shows that key success merging titanium-mediated homolysis alcoholic C–O bonds olefin difunctionalization.

Язык: Английский

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N-Arylation of Amino Acid Esters via an I₂-Mediated Metal-Free Multicomponent Benzannulation Strategy

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16649 - 16654

Опубликована: Ноя. 15, 2023

Herein, we present a novel method for the N-arylation of amino acid esters using α-bromoacetaldehyde acetal and acetoacetate via an I2-mediated metal-free benzannulation strategy, which disclosed first synthetic application acids nonaromatic building blocks. The synthesized N-arylated derivatives were found to possess promising selective inhibition against human hepatocellular liver carcinoma cells, melanoma normal with IC50 value as low 16.79 μg·mL-1.

Язык: Английский

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Palladium-catalyzed cyclization borylmethylation: Access to boryl-functionalized benzene-fused heterocycle compounds

Tetrahedron Letters, Год журнала: 2024, Номер 148, С. 155216 - 155216

Опубликована: Авг. 3, 2024

Язык: Английский

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Reductive Dicarbofunctionalization of C–C π-Bonds

Elsevier eBooks, Год журнала: 2023, Номер unknown

Опубликована: Янв. 1, 2023

Язык: Английский

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