Direct arylation of strong aliphatic C–H bonds

Nature, Год журнала: 2018, Номер 560(7716), С. 70 - 75

Опубликована: Июль 24, 2018

Язык: Английский

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Toolbox for Distal C–H Bond Functionalizations in Organic Molecules

Chemical Reviews, Год журнала: 2021, Номер 122(6), С. 5682 - 5841

Опубликована: Окт. 18, 2021

Transition-metal-catalyzed C–H activation has developed a contemporary approach to the omnipresent area of retrosynthetic disconnection. Scientific researchers have been tempted take help this methodology plan their synthetic discourses. This paradigm shift helped in development industrial units as well, making synthesis natural products and pharmaceutical drugs step-economical. In vast zone bond activation, functionalization proximal bonds gained utmost popularity. Unlike bonds, distal is more strenuous requires distinctly specialized techniques. review, we compiled various methods adopted functionalize mechanistic insights within each these procedures, scope methodology. With give complete overview expeditious progress made field organic chemistry while also highlighting its pitfalls, thus leaving open for further modifications.

Язык: Английский

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Transition-Metal-Catalyzed C–H Bond Activation for the Formation of C–C Bonds in Complex Molecules

Chemical Reviews, Год журнала: 2023, Номер 123(12), С. 7692 - 7760

Опубликована: Май 10, 2023

Site-predictable and chemoselective C–H bond functionalization reactions offer synthetically powerful strategies for the step-economic diversification of both feedstock fine chemicals. Many transition-metal-catalyzed methods have emerged selective activation bonds. However, challenges regio- chemoselectivity with application to highly complex molecules bearing significant functional group density diversity. As molecular complexity increases within structures risks catalyst intolerance limited applicability grow number groups potentially Lewis basic heteroatoms. Given abundance bonds already diversified such as pharmaceuticals, natural products, materials, design selection reaction conditions tolerant catalysts has proved critical successful direct functionalization. such, innovations formation carbon–carbon been discovered developed overcome these limitations. This review highlights progress made metal-catalyzed C–C forming including alkylation, methylation, arylation, olefination targets.

Язык: Английский

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Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

Chemical Reviews, Год журнала: 2020, Номер 120(13), С. 6124 - 6196

Опубликована: Июнь 3, 2020

A critically important process in catalysis is the formation of an active catalyst from combination a metal precursor and ligand, as efficacy this reaction governs amount catalyst. This Review comprehensive overview reactions catalyzed by nickel added bidentate phosphine, focusing on steps transforming precatalyst ligand into potential effects transformation catalysis. Reactions covered include common cross-coupling reactions, such Suzuki, Heck, Kumada, Negishi couplings, addition cycloadditions, C–H functionalizations, polymerizations, hydrogenations, reductive among others. Overall, most widely used with free phosphines Ni(cod)2, which accounts for ∼50% reports surveyed, distantly followed Ni(acac)2 Ni(OAc)2, account ∼10% each. By compiling these we have calculated statistics usage each Ni(cod)2 other sources. The are simple, relatively inexpensive ligands, DPPE, DCPE, DPPP, DPPB, along others more complex backbones, DPPF Xantphos. use expensive chiral scattered, but ligands BINAP, Me-Duphos, Josiphos, related analogs.

Язык: Английский

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Nickel-catalyzed formation of quaternary carbon centers using tertiary alkyl electrophiles

Chemical Society Reviews, Год журнала: 2021, Номер 50(6), С. 4162 - 4184

Опубликована: Янв. 1, 2021

This review provides a comprehensive summary of recent advances in nickel-catalyzed reactions employing tertiary alkyl electrophiles for the construction quaternary carbon centers.

Язык: Английский

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Photoactive electron donor–acceptor complex platform for Ni-mediated C(sp³)–C(sp²) bond formation

Chemical Science, Год журнала: 2021, Номер 12(15), С. 5450 - 5457

Опубликована: Янв. 1, 2021

This works demonstrates the implementation of an electron donor–acceptor (EDA) complex platform toward Ni-catalyzed C(sp³)–C(sp²) bond formation, circumventing need for exogenous photocatalysts, additives, and stoichiometric metal reductants.

Язык: Английский

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Emerging Trends in Cross-Coupling: Twelve-Electron-Based L₁Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications

Chemical Reviews, Год журнала: 2022, Номер 122(23), С. 16983 - 17027

Опубликована: Окт. 3, 2022

Monoligated palladium(0) species, L

Язык: Английский

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Desulfonylative Transformations of Sulfones by Transition-Metal Catalysis, Photocatalysis, and Organocatalysis

ACS Catalysis, Год журнала: 2022, Номер 12(5), С. 3013 - 3032

Опубликована: Фев. 18, 2022

Sulfones are common, readily available reagents that have recently attracted attention as versatile for cross-coupling reactions. This Review summarizes advances in desulfonylative transformations of sulfones affected by molecular catalysis, including transition-metal catalysts, photocatalysts, and organocatalysts. In addition to catalyst choice, the design sulfonyl group is a critical factor control reactivity. The concepts presented herein will provide new strategies construct diverse molecules with high efficiency modularity.

Язык: Английский

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Decarboxylative Borylation and Cross-Coupling of (Hetero)aryl Acids Enabled by Copper Charge Transfer Catalysis

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(14), С. 6163 - 6172

Опубликована: Апрель 4, 2022

We report a copper-catalyzed strategy for arylboronic ester synthesis that exploits photoinduced ligand-to-metal charge transfer (LMCT) to convert (hetero)aryl acids into aryl radicals amenable ambient-temperature borylation. This near-UV process occurs under mild conditions, requires no prefunctionalization of the native acid, and operates broadly across diverse aryl, heteroaryl, pharmaceutical substrates. also one-pot procedure decarboxylative cross-coupling merges catalytic LMCT borylation palladium-catalyzed Suzuki-Miyaura arylation, vinylation, or alkylation with organobromides access range value-added products. The utility these protocols is highlighted through development heteroselective double-decarboxylative C(sp2)-C(sp2) coupling sequence, pairing halogenation processes two distinct (including substrates) subsequent cross-coupling.

Язык: Английский

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Iron-catalysed reductive cross-coupling of glycosyl radicals for the stereoselective synthesis of C-glycosides

Nature Synthesis, Год журнала: 2022, Номер 1(3), С. 235 - 244

Опубликована: Фев. 17, 2022

Язык: Английский

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