4.6 Article

Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent

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。
Article Chemistry, Organic

Visible-Light-Induced para-Difluoroalkylation of Aniline Derivatives

Xipeng Jiang et al.

Summary: A visible-light-induced, iridium catalyzed, para-selective C-H difluoroalkylation of aniline derivatives under mild reaction conditions is reported. This protocol features a wide substrate scope, high regioselectivity, low catalyst usage, and operational simplicity.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Chemistry, Analytical

The Role of 8-Amidoquinoline Derivatives as Fluorescent Probes for Zinc Ion Determination

Nur Syamimi Mohamad et al.

Summary: This review discusses the use of 8-aminoquinoline and its derivatives as zinc ion receptors for sensor probes. The introduction of various carboxamide groups into 8-aminoquinoline molecules to create 8-amidoquinoline derivatives has been a recent trend.

SENSORS (2021)

Article Chemistry, Organic

Iron-Catalyzed Remote C-H Alkylation of 8-Amidoquinolines with Cycloalkanes

Wengang Xu et al.

Summary: A new iron-catalyzed method has been developed for the site-selective alkylation of the quinoline nucleus, which shows good efficiency in producing C5-alkylation products. Based on control experiments, a proposed reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate.

SYNTHESIS-STUTTGART (2021)

Article Chemistry, Organic

Electrolyte-Triggered C5-Selective Trifluoromethylation and Halogenation of 8-Aminoquinoline Derivatives

Kai Wang et al.

Summary: An efficient electrolyte-triggered trifluoromethylation and halogenation at C5 position of 8-aminoquinoline derivatives was developed, giving moderate to excellent yields of C-H functionalization products. The mild and green reactions had lower energy consumption and shorter reaction times, while avoiding the use of transition-metal catalysts and oxidants.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

A Guide to Directing Group Removal: 8-Aminoquinoline

Liam S. Fitzgerald et al.

Summary: This review discusses strategies for efficient removal of directing groups, focusing on the widely used N,N-bidentate directing group 8-aminoquinoline. The limitations of these strategies and alternative approaches for challenging substrates are also discussed. The aim is to provide a comprehensive guide for chemists in academia and industry to harness the synthetic power of directing groups and remove them from final products.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Organic

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Feng Liu et al.

Summary: This study introduces a new protocol that combines the efficiency of electrochemical transformation and the high reactivity of chlorine, utilizing Cl3CCN as the chloride source to achieve chlorination of aromatic compounds and electrodeficient alkenes.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Transition-Metal-Free Cross-Dehydrogenative Couplings of 8-Aminoquinoline Amides at C5 Position with Acetonitrile, Ethers or Acetone

Da Liu et al.

Summary: A novel and efficient method has been developed for highly regioselective cyanomethylation of 8-aminoquinoline amides at the C5 position, under transition metal-free and base-free conditions. This protocol offers simple operation, high efficiency, good functional group tolerance, and broad substrate scope. Additionally, etherification or acetonation products can be obtained when acetonitrile is replaced by ethers or acetone, with a radical process involved in the reaction.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Merging Photoredox Catalysis with Transition Metal Catalysis: Direct C4-H Sulfamidation of 1-Naphthylamine Derivatives

Mengxue Pei et al.

Summary: This study successfully achieved the C4-H sulfamidation of 1-naphthylamine derivatives with NHSI catalyzed by copper(I) under mild conditions, yielding moderate to good results. Control experiments suggested that the visible-light-promoted reaction might proceed through a single-electron-transfer process, and preliminary DFT studies on intermediates supported the plausible mechanism, with the C4 site in the naphthyl ring identified as the most likely electrophilic reactive site.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Biochemistry & Molecular Biology

Regioselective Functionalization of Quinolines through C-H Activation: A Comprehensive Review

Alessandra Corio et al.

Summary: Quinoline is a versatile heterocycle found in natural products and drugs, and is widely used as a ligand in organometallic catalysis. Efforts have been focused on developing efficient and regioselective synthetic methods for functionalized quinolines, with C-H functionalization through transition metal catalysis being the most attractive strategy. This review aims to provide a comprehensive overview of methods for selective metal-catalyzed C-H functionalization of quinolines, focusing on their scope, limitations, and mechanistic aspects.

MOLECULES (2021)

Article Chemistry, Organic

Bromination of phenyl ether and other aromatics with bromoisobutyrate and dimethyl sulfoxide

Jia-Qin Li et al.

Summary: Bromoisobutyrate is utilized for the first time as a brominating source in the direct bromination of various simple phenyl ethers, yielding brominated arenes in moderate to good yields for compounds with different substitutions. The reaction system can be extended to phenols and unactivated arenes, serving as an alternative to established bromination systems for bromoarene synthesis.

TETRAHEDRON LETTERS (2021)

Article Chemistry, Multidisciplinary

Direct Phase-Transition Catalysed Monohalogenation of 8-Amidoquinolines at C5 Position in Water

Xin He et al.

Summary: A novel protocol for direct halogenation of 8-amidoquinoline derivatives using water as solvent and achieving C5-halogenation products at room temperature was reported. The reactions were promoted by benzyltriethylammonium chloride and dihalogenated hydantoin.

CHEMISTRYSELECT (2021)

Article Chemistry, Organic

C-5 selective chlorination of 8-aminoquinoline amides using dichloromethane

Xinxin Lin et al.

Summary: An oxidant-free electrochemical regioselective chlorination of 8-aminoquinoline amides was achieved at ambient temperature in batch and continuous-flow setups, using inert DCM as the chlorinating reagent. The method allows for convenient scale up with higher productivity, good position control, and tolerance to water and air. Costly quaternary ammonium salts were avoided, and various experiments were conducted to gain insight into the reaction mechanism.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of 2-phenyl-4-aminoquinolines as potential antifungal agents

Rui Yang et al.

MOLECULAR DIVERSITY (2020)

Review Chemistry, Multidisciplinary

Remote C-H Functionalization of 8-Aminoquinoline Ring

Zhihui Xu et al.

TOPICS IN CURRENT CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Three-component ruthenium-catalyzed remote C-H functionalization of 8-aminoquinoline amides

Wei-Yu Shi et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Organic

Metal-Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions UsingN-Halosuccinimides

Jiahao Hou et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile

Chunxia Wen et al.

CHEMICAL COMMUNICATIONS (2020)

Review Chemistry, Applied

Base Metal Catalysis in Directed C(sp3)-H Functionalisation

Sahra St John-Campbell et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Article Chemistry, Applied

Copper-Catalyzed C-4 Carboxylation of 1-Naphthylamide Derivatives with CBr4/MeOH

Tapan Sahoo et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Review Microbiology

8-Aminoquinoline Therapy for Latent Malaria

J. Kevin Baird

CLINICAL MICROBIOLOGY REVIEWS (2019)

Article Chemistry, Multidisciplinary

Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane

Yujie Liang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Organic

Ruthenium-catalyzed remote C5-sulfonation of N-alkyl-8-aminoquinolines

Xuri Liu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Physical

Methoxylation on the C5 and C6 positions of quinolines with methanol

Guodong Wang et al.

CATALYSIS COMMUNICATIONS (2018)

Article Chemistry, Organic

Transition-Metal-Free Regioselective C-H Bond Fluorination of 8-Amidoquinolines with Selectfluor

Hao Chen et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Transition metal free oxygenation of 8-aminoquinoline amides in water

Xinghui Yao et al.

GREEN CHEMISTRY (2018)

Article Chemistry, Organic

Remote alkylation of N-(quinolin-8-yl)benzamides with alkyl bromides via ruthenium(II)-catalyzed C-H bond activation

Arumugam Mariappan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

Damoder Reddy Motati et al.

CHEMICAL SCIENCE (2018)

Review Chemistry, Organic

Remote C-H Functionalization of 8-Aminoquinolinamides

Bhuttu Khan et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Pharmacology & Pharmacy

Tafenoquine: First Global Approval

James E. Frampton

Article Chemistry, Organic

Copper-Catalyzed C5-H Sulfenylation of Unprotected 8-Aminoquinolines Using Sulfonyl Hydrazides

Qing Yu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Applied

Copper-Catalyzed Remote C-H Amination of Quinolines with N-Fluorobenzenesulfonimide

Yao Yin et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Article Chemistry, Organic

Ruthenium-Catalyzed Difluoroalkylation of 8-Aminoquinoline Amides at the C5-Position

Changpeng Chen et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Organic

Iron-mediated remote C-H bond benzylation of 8-aminoquinoline amides

Mian Cui et al.

TETRAHEDRON LETTERS (2017)

Article Chemistry, Organic

Copper- catalyzed C5-selective thio/selenocyanation of 8-aminoquinolines

Jichao Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Article Chemistry, Organic

Nickel-catalyzed selective C-5 fluorination of 8-aminoquinolines with NFSI

Junshuai Ding et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Remote C-H Sulfonylation of 8-Aminoquinoline Amides with Arylsulfonyl Hydrazides

Guoshu Chen et al.

CHEMISTRYSELECT (2017)

Review Chemistry, Organic

Recent Advances on the C-H Bond Functionalization on C(5) Position of 8-Aminoquinolines

Longzhi Zhu et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Coordination strategy-induced selective C-H amination of 8-aminoquinolines

Hong Yi et al.

CHEMICAL COMMUNICATIONS (2017)

Article Chemistry, Applied

Copper-Catalyzed Remote C-H Functionalization of 8-Aminoquinolines with Sodium and Lithium Sulfinates

Shuai Liang et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Silver-Mediated Intermolecular 1,2-Alkylarylation of Styrenes with -Carbonyl Alkyl Bromides and Indoles

Xuan-Hui Ouyang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Palladium-catalyzed cross-coupling of enamides with sterically hindered α-bromocarbonyls

Ran Ding et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Organic

Copper-Catalyzed Regioselective C-H Sulfonylation of 8-Aminoquinolines

Jun Wei et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Medicinal

Developing structure-activity relationships from an HTS hit for inhibition of the Cks1-Skp2 protein-protein interaction

Rajinder Singh et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2015)

Article Chemistry, Organic

Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position

Longzhi Zhu et al.

ORGANIC LETTERS (2015)

Review Chemistry, Organic

Reusable and Removable Directing Groups for C(sp2)-H Bond Functionalization of Arenes

M. Ramu Yadav et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2015)

Review Chemistry, Organic

Transition-Metal-Catalyzed Arylation of Unactivated C(sp3)-H Bonds Assisted by Bidentate Directing Groups

Bo Zhang et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2014)

Review Chemistry, Multidisciplinary

Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups

Guy Rouquet et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C-H Oxidation

Alison M. Suess et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

New Anthraquinone Dyes with Different Side Group Positions for LCD Color Filters

Sola Lee et al.

MOLECULAR CRYSTALS AND LIQUID CRYSTALS (2013)

Article Agronomy

Effect of Postflood Quinclorac Applications on Commercial Rice Cultivars

Jason A. Bond et al.

WEED TECHNOLOGY (2012)

Article Chemistry, Multidisciplinary

The Ammosamides: Structures of Cell Cycle Modulators from a Marine-Derived Streptomyces Species

Chambers C. Hughes et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Medicinal

Primaquine revisited six decades after its discovery

Nuno Vale et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2009)

Article Chemistry, Multidisciplinary

Highly regloselective arylation of Sp3 C-H bonds catalyzed by palladium acetate

VG Zaitsev et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Review Multidisciplinary Sciences

Understanding and exploiting C-H bond activation

JA Labinger et al.

NATURE (2002)