4.7 Article

Hydropyridylation of α,β-Unsaturated Esters through Electroreduction of 4-Cyanopyridine

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Electrochemical Ammonium Cation-Assisted Hydropyridylation of Ketone-Activated Alkenes: Experimental and Computational Mechanistic Studies

Jianjing Yang et al.

Summary: This work describes an electrochemical method for hydropyridylation of ketone-activated alkenes using ammonium cation, giving access to beta-pyridyl ketones. The method features a broad substrate scope and gram-scale synthesis, with ammonium chloride playing various roles in the transformation. Experiments and DFT calculations confirm the mechanism of dual proton-coupled electron transfer followed by radical cross-coupling as the preferred pathway.

ADVANCED SYNTHESIS & CATALYSIS (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, Organic

Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling

Hehuan Xu et al.

Summary: An electrochemical method has been developed for the hydropyridylation of thioester-activated alkenes with 4-cyanopyridines. The reactions involve tandem electroreduction, protonation, and radical cross-coupling processes, resulting in a variety of valuable pyridine derivatives with tertiary or quaternary carbons at the alpha position. The use of thioesters eliminates the need for catalysts and high temperatures, making it a highly sustainable synthetic approach.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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: Expanding the Scope of Paired Reactions

Tiandi Wu et al.

Summary: Paired electrochemical reactions allow for optimization of atom and energy economy of oxidation and reduction reactions by adjusting the potentials at both electrodes, with substrate matching not being necessary. Any oxidation reaction can theoretically be paired with any reduction reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (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, Multidisciplinary

Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics

Jin-Lin Wan et al.

Summary: In this study, iminyl radicals were generated through the electrochemical decarboxylation of alpha-imino-oxy acids using nBu(4)NBr as a mediator under exogenous-oxidant- and metal-free conditions. These iminyl radicals underwent intramolecular cyclization smoothly with adjacent (hetero)arenes to form a series of indole-fused polycyclic compounds.

CHEMICAL COMMUNICATIONS (2021)

Review Chemistry, Multidisciplinary

Recent advances in electrochemical oxidative cross-coupling with hydrogen evolution involving radicals

Yong Yuan et al.

Summary: Oxidative cross-coupling is a robust method for forming C-C, C-X, and X-Y bonds. Organic electrosynthesis is recognized as an environmentally friendly and powerful synthetic platform. Recent advancements have shown that radical-involved electrochemical oxidative cross-coupling reactions can be achieved under exogenous-oxidant-free conditions.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Multidisciplinary

Recent advances in the radical-mediated decyanative alkylation of cyano(hetero)arene

Shiqi Tong et al.

Summary: The article summarizes recent advances in the radical-mediated decyanative alkylation reactions of cyano(hetero)arene via photo/electrochemistry, discussing the mechanisms involved in cleaving C(sp3)-H, C(sp2)-H, C-C or C-hetero bonds and forming new C-C bonds.

GREEN SYNTHESIS AND CATALYSIS (2021)

Article Chemistry, Organic

Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes

Jiaxuan Shen et al.

Summary: The reported reaction utilizes organic photoredox catalysis to achieve intermolecular pyridylation/phosphinoylation of alkenes, with broad substrate scope under mild metal-free conditions, suitable for gram-scale production and modification of medicinal molecules. Mechanistic investigations indicate that triethylamine functions as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents in the reaction.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Multidisciplinary

Organic-photoredox-catalyzed three-component sulfonylative pyridylation of styrenes

Fang Wang et al.

Summary: An efficient metal-free protocol for the three-component sulfonylative pyridylation of styrenes via organic-photoredox catalysis has been described. This process enables the direct and selective installation of sulfonyl and heteroaryl motifs, tolerating a wide range of functional groups and complex molecular scaffolds. It could complement previous methods and be of interest in pharmaceutical research.

RSC ADVANCES (2021)

Review Chemistry, Multidisciplinary

The Persistent Radical Effect in Organic Synthesis

Dirk Leifert et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Electrochemistry

Basic Strategies and Types of Applications in Organic Electrochemistry

Gerhard Hilt

CHEMELECTROCHEM (2020)

Review Chemistry, Multidisciplinary

From Molecules to Molecular Surfaces. Exploiting the Interplay Between Organic Synthesis and Electrochemistry

Qiwei Jing et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Review Chemistry, Multidisciplinary

A Decade of Electrochemical Dehydrogenative C,C-Coupling of Aryls

Johannes L. Roeckl et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Nickel(0)-Catalyzed Enantioselective [3+2] Annulation of Cyclopropenones and α,β-Unsaturated Ketones/Imines

Dachang Bai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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

Synthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox Catalysis

Michael C. Nicastri 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 Multidisciplinary Sciences

Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine

Shengqing Zhu et al.

NATURE COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Intermolecular, redox-neutral azidoarylation of alkenes via photoredox catalysis

Jian Chen et al.

CHEMICAL COMMUNICATIONS (2019)

Review Chemistry, Multidisciplinary

Renaissance of pyridine-oxazolines as chiral ligands for asymmetric catalysis

Guoqiang Yang et al.

CHEMICAL SOCIETY REVIEWS (2018)

Article Chemistry, Physical

An Electrocatalytic Approach to the Radical Difunctionalization of Alkenes

Gregory S. Sauer et al.

ACS CATALYSIS (2018)

Review Chemistry, Multidisciplinary

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

Yangye Jiang et al.

CHEMICAL REVIEWS (2018)

Review Chemistry, Multidisciplinary

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Ming Yan et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Inorganic & Nuclear

Pyridine and Related Ligands in Transition Metal Homogeneous Catalysis

M. N. Zafar et al.

RUSSIAN JOURNAL OF COORDINATION CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D

Jiun-Le Shih et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Multidisciplinary Sciences

The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis

James D. Cuthbertson et al.

NATURE (2015)

Review Chemistry, Multidisciplinary

Redox catalysis in organic electrosynthesis: basic principles and recent developments

Robert Francke et al.

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Multidisciplinary

Decarboxylative Arylation of α-Amino Acids via Photoredox Catalysis: A One-Step Conversion of Biomass to Drug Pharmacophore

Zhiwei Zuo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Electrochemical Allylation Reactions of Simple Imines in Aqueous Solution Mediated by Nanoscale Zinc Architectures

Jing-Mei Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives

Jie Sun et al.

CHINESE CHEMICAL LETTERS (2011)

Review Chemistry, Multidisciplinary

Modern strategies in electroorganic synthesis

Jun-ichi Yoshida et al.

CHEMICAL REVIEWS (2008)

Article Chemistry, Multidisciplinary

Oxygen and base-free oxidative heck reactions of arylboronic acids with olefins

Jiwu Ruan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)