4.8 Article

Scandium-Catalyzed Electrochemical Synthesis of α-Pyridinyl Tertiary Amino Acids and Esters

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Review Chemistry, Multidisciplinary

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Nicholas E. S. Tay et al.

Summary: Redox processes play a crucial role in synthetic methods involving electrochemistry and photoredox catalysis. Both approaches offer access to high energy intermediates that allow for unconventional bond formations. However, while they provide similar intermediates, electrochemistry and photoredox catalysis differ in their physical chemistry principles. Understanding these differences is essential for designing new transformations and bond disconnections.

CHEMICAL REVIEWS (2022)

Article Multidisciplinary Sciences

Insertion of ammonia into alkenes to build aromatic N-heterocycles

Shuai Liu et al.

Summary: The authors demonstrate a novel methodology for the synthesis of aromatic heterocycles containing nitrogen by electrochemically inserting nitrogen atoms into a carbon ring using ammonia. This approach offers high atom and step economy, making it valuable for extensive applications in chemical and biological research, with significant potential for drug development.

NATURE COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis

Xu Cheng et al.

Summary: This review presents recent advances in electrochemical homogeneous catalysis, with a focus on electrochemical noble-transition-metal catalysis, photoelectrochemical catalysis, and electrochemical enantioselective catalysis. The topics discussed include the mechanism of noble metal catalysts in the presence of cathodic hydrogen evolution, the enhancement of redox properties in photocatalysis, and the regulation of enantioselectivity in catalytic electrochemical reactions.

CCS CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Electrochemical Aziridination of Tetrasubstituted Alkenes with Ammonia

Shuai Liu et al.

Summary: Ammonia is an ideal nitrogen source with high availability, reactivity, safety, atom economy, environmental compatibility, and ease of isolation. However, its utility for amine synthesis is limited by its high bond dissociation energy, strong coordination ability, and difference in reactivity compared to the product amines.

CCS CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Reductive Azaarylation of Olefins via Enantioselective Radical Coupling

Yajuan Li et al.

Summary: Visible-light-driven photocatalytic reductive azaarylation is widely used for the construction of imine-containing azaarene derivatives. Although efficient methods have been established, enantioselective reactions remain a challenge. This study demonstrates the feasibility of chiral hydrogen-bonding/photosensitizer catalysis for achieving enantioselective reductive azaarylation, leading to valuable enantioenriched azaarene variants.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Multidisciplinary Sciences

Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction

Weijie Ding et al.

Summary: In this study, we propose a new method for catalytic asymmetric allylic 4-pyridinylation reactions using 4-CN-pyridine under electrochemical conditions. This method has significant scientific and practical implications.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Organic

Electroreductive 4-pyridylation of unsaturated compounds using gaseous ammonia as a hydrogen source

Weijie Ding et al.

Summary: This study reports an electrochemical radical-cross-coupling reaction using ammonia as a terminal reductant in the reactions between various esters and ketones with 4-CN pyridine. More than 50 pyridylation products were synthesized using constant current conditions and thiourea as a promoter to activate the intermediate derived from 4-CN pyridine.

ORGANIC CHEMISTRY FRONTIERS (2022)

Review Chemistry, Multidisciplinary

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Guglielmo A. Coppola et al.

Summary: Visible-light photoredox catalysis and organic electrochemistry are important tools in organic synthesis, providing alternative routes with higher selectivity and broader applicability. These two fields have great research value and are making continuous progress.

CHEMICAL SOCIETY REVIEWS (2022)

Article Chemistry, Organic

Electroreductive C3 Pyridylation of Quinoxalin-2(1H)-ones: An Effective Way to Access Bidentate Nitrogen Ligands

Jiangwei Wen et al.

Summary: The electroreductive-induced C3 pyridylation of quinoxalin-2(1H)-ones with cyanopyridines provides a convenient, efficient, and gram-scale synthesis strategy for a series of new types of potential bidentate nitrogen ligands, achieving yields of over 95% in more than 36 examples.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Electrochemical Aziridination of Internal Alkenes with Primary Amines

Maksim Oseka et al.

Summary: Aziridines are important synthetic building blocks in organic synthesis and the effective coupling of alkenes and amines has been achieved using an electrochemical approach. This study presents a new strategy for the efficient synthesis of aziridines, with short reaction times, high yields, and broad substrate scope. The mechanistic investigations and DFT calculations provide insight into the reaction mechanism involving oxidative coupling of alkenes and primary alkylamines.
Article Chemistry, Physical

Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids

Jiale Shi et al.

Summary: A protocol utilizing metal-free ceramic BCN for the photocatalytic decarboxylation of carboxylic acids has been developed, demonstrating efficient formation of carbon-centered radicals and carbon-carbon bonds, showing practicality and wide application prospects.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Organic Electrochemistry: Molecular Syntheses with Potential

Cuiju Zhu et al.

Summary: Organic electrosynthesis has emerged as a sustainable platform for molecular assembly, showcasing exceptional selectivities, synergies with photocatalysis or dual electrocatalysis, and novel mechanisms in metallaelectrocatalysis.

ACS CENTRAL SCIENCE (2021)

Article Chemistry, Organic

Reductive Arylation of Aliphatic and Aromatic Aldehydes with Cyanoarenes by Electrolysis for the Synthesis of Alcohols

Xiao Zhang et al.

Summary: An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well as ketones with electro-deficient (hetero)arenes is described, providing secondary and tertiary alcohols in moderate to good yields. Mechanistic studies support the generation of aliphatic ketyl radicals and persistent heteroaryl radical anions via cathodic reduction followed by radical-radical cross-coupling.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Electrochemical Tandem Olefination and Hydrogenation Reaction with Ammonia

Xiaofeng Zhang et al.

Summary: An electrochemical tandem reaction utilizing ammonia as electron and proton donors was successfully achieved, leading to the formation of two-carbon-elongated ester and nitrile from aldehyde or ketones. The reaction could proceed with a catalytic amount of base or even without a base, demonstrating the versatility and efficiency of this method.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Direct Electrocatalytic N-H Aziridination of Aromatic Alkenes Using Ammonia

Jef R. Vanhoof et al.

Summary: The study reported a method for electrocatalytic N-H aziridination of simple aromatic alkenes using ammonia as a nitrogen source, achieving high yields up to 98% with H-2 as the only byproduct. The use of iodide as a redox mediator was essential for obtaining the desired products, with mechanistic studies revealing the formation of NH2I as a reactive species involved in the aziridination.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

Review Chemistry, Multidisciplinary

Electrocatalysis as an enabling technology for organic synthesis

Luiz F. T. Novaes et al.

Summary: Electrochemistry has recently become a versatile strategy in achieving challenging transformations in synthetic organic chemistry. The use of redox-active electrocatalysts has increased in recent developments in electrosynthesis to enhance control over reactive intermediates. Electrocatalytic mediators allow for synthetic transformations to proceed in a manner different from purely chemical methods.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Organic

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Liu Chang et al.

Summary: This study presents an electrochemical reduction method for nitroarenes using inert graphite felt as electrodes and ammonia as a reductant. By adjusting the cell voltage and solvent, different nitrogen-containing aromatic compounds can be selectively synthesized, and the reaction can be scaled up to over 10 grams with no decrease in yield. A stepwise cathodic reduction pathway is proposed to explain the generation of products.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Electrochemical Synthesis of Hindered Primary and Secondary Amines via Proton-Coupled Electron Transfer

Dan Lehnherr et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

New Radical Borylation Pathways for Organoboron Synthesis Enabled by Photoredox Catalysis

Jing Qi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

Benjamin Lipp et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Multidisciplinary

Electrochemical Hydrogenation with Gaseous Ammonia

Jin Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Reagent-Free C-H/N-H Cross-Coupling: Regioselective Synthesis of N-Heteroaromatics from Biaryl Aldehydes and NH3

Huai-Bo Zhao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp2)-C(sp3) Cross-Couplings in Flow

Fabio Lima et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Medicinal

1,4-Oxazine β-Secretase 1 (BACE1) Inhibitors: From Hit Generation to Orally Bioavailable Brain Penetrant Leads

Frederik J. R. Rombouts et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Arylcyanation of norbornene and norbornadiene catalyzed by nickel

Yoshiaki Nakao et al.

CHEMISTRY LETTERS (2006)