Highly Regioselective Synthesis of N-β-trifluoromethyl 2-pyridones via anti-Markovnikov Hydroamination of α-(trifluoromethyl)styrenes with 2-pyridones

Review Chemistry, Applied

Recent Advances in the Synthesis of Difluorinated Architectures from Trifluoromethyl Groups

Feng Zhao et al.

Summary: This review summarizes the recent developments of new methods for the synthesis of difluoromethyl motifs or difluoroalkenes from trifluoromethylated aromatic compounds or trifluoromethyl alkenes via single C(sp(3))-F bond cleavage.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Advances in cycloaddition and hydroaddition reaction of α-(trifluoromethyl)styrenes without defluorination: An alternative approach to CF3-containing compounds

Yupian Deng et al.

Summary: Alpha-(trifluoromethyl)styrene and its derivatives are widely used in pharmaceuticals, agrochemicals, and advanced materials. They are versatile building blocks for the preparation of various compounds. Recent efforts have focused on developing reactions for accessing gem-difluoroalkenes and gem-difluoroalkylated compounds without defluorination. However, the use of alpha-(trifluoromethyl)styrenes in cycloaddition and hydroaddition reactions while retaining three C-F bonds remains underdeveloped.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

1,2-Dicarbofunctionalization of Trifluoromethyl Alkenes with Pyridinium Salts via a Cycloaddition/Visible-Light-Enabled Fragmentation Cascade

Shu-Jie Chen et al.

Summary: This Letter presents a novel approach for the 1,2-dicarbofunctionalization of trifluoromethyl alkenes. The method involves a cascade reaction of pyridinium salts with trifluoromethyl alkenes, leading to the formation of pyridines bearing a trifluoromethyl-substituted quaternary center.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Rhodium-catalyzed dearomative rearrangement of 2-oxypyridines with cyclopropenes: access to N-alkylated 2-pyridones

Honglian Cui et al.

Summary: A new rhodium-catalyzed reaction has been developed using cyclopropenes as carbene precursors, enabling the synthesis of 2-alkylated 2-pyridone derivatives from 2-oxypyridines. This method offers broad substrate scope, mild reaction conditions and a reliable approach for the efficient synthesis of the desired compounds.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Organic

Tunable photocatalytic oxysulfonylation and chlorosulfonylation of α-CF3 alkenes with sulfonyl chlorides

Peng-Ju Xia et al.

Summary: This strategy utilizes tunable photoredox catalysis and manipulation of catalyst and solvent to achieve chlorosulfonylation and oxysulfonylation of alpha-trifluoromethylstyrenes, resulting in diverse bifunctional products with up to 95% yield and excellent functional group tolerance.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Review Chemistry, Organic

Multiple-fold C-F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle

Danhua Ge et al.

Summary: This review aims to highlight the recent advances in C-F bond activation and heterocyclic chemistry, with a focus on the control of reaction selectivity and pathways in poly- or perfluorine-containing compounds through the cleavage of C-F bonds.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Organic

Defluorinative C-C Bond-Forming Reaction of Trifluoromethyl Alkenes with gem-(Diborylalkyl)lithiums

Haeun Kim et al.

Summary: In this study, we achieved a transition-metal-free defluorinative C-C bond-forming reaction between trifluoromethyl alkenes and gem-(diborylalkyl)lithiums. This synthetic strategy allows the synthesis of a variety of 4,4-difluoro homoallylic diboronate esters, which are valuable intermediates for the efficient preparation of gem-difluoroalkene derivatives. Further synthetic modifications were performed to demonstrate the synthetic utility of the obtained 4,4-difluoro homoallylic diboronate esters.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

DBN-Mediated Addition Reaction of α-(Trifluoromethyl)styrenes with Diazoles, Triazoles, Tetrazoles, and Primary, Secondary, and Secondary Cyclic Amines

Jingjing He et al.

Summary: A mild and efficient DBN-mediated addition reaction was developed for the synthesis of various β-trifluoromethyl nitrogen-containing heterocycles and β-trifluoromethyl amines using α-(trifluoromethyl)styrenes and diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic amines.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Ni-Catalyzed Radical-Promoted Defluoroalkylborylation of Trifluoromethyl Alkenes To Access gem-Difluorohomoallylic Boronates

Jian Qiu et al.

Summary: In this study, an efficient protocol for the construction of gem-difluorohomoallylic boronates was developed through a nickel-catalyzed radical promoted defluoroalkylborylation reaction under mild conditions, using α-trifluoromethyl alkenes and α-haloboronates as substrates. This reaction demonstrated a broad substrate scope, good functional group tolerance, and diverse transformations.

ORGANIC LETTERS (2022)

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Article Chemistry, Applied

Iridium-Catalyzed Intermolecular Asymmetric Allylic Amination with Pyridones

Hang-Fei Tu et al.

Summary: We report a catalytic synthetic method for enantioenriched N-substituted pyridones in this study. By using a chiral iridium catalyst generated from the Carreira [P/olefin] ligand, intermolecular asymmetric allylic amination between allyl alcohols and pyridones proceeded smoothly with excellent chemo-, regio-, and enantioselectivities. This method displayed a broad substrate scope for both pyridones and allylic alcohols and showed potential for diverse transformations of the amination products to useful skeletons.

ADVANCED SYNTHESIS & CATALYSIS (2022)

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Article Chemistry, Organic

Bifunctional Lewis Base Catalyzed Asymmetric N-Allylic Alkylation of 2-Hydroxypyridines

Fei-Ruo Zhang et al.

Summary: A chiral Lewis base catalyzed enantioselective N-allylic alkylation reaction of 2-hydroxypyridines has been documented, leading to the convenient synthesis of N-alkylated 2-pyridones with high enantioselectivity and yield. Experimental and computational studies reveal that the strong hydrogen bond interaction between the chiral Lewis base catalyst and 2-hydroxypyridines is crucial for the reactivity, chemoselectivity, and enantioselectivity of this reaction.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Selective C-F Bond Etherification of Trifluoromethylalkenes with Phenols

Qingqiang Tian et al.

Summary: A novel protocol for selective C-F bond etherification of trifluoromethylalkenes and phenols has been reported, generating the pharmaceutically privileged difluoromethylene moiety. DFT calculation results and control experiments suggest the involvement of metal ion Cs+ in the defluorooxylation process. Furthermore, the obtained product exhibits good insecticidal activity.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates

Ming Hu et al.

Summary: Selective defluoroborylation and asymmetric hydro-boration reactions have been developed for fluoroalkyl-substituted terminal alkenes, resulting in the synthesis of chiral alkylboronates with fluoroalkyl-substituted stereogenic carbon centers.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Physical

Nickel-Catalyzed anti-Markovnikov Hydroalkylation of Trifluoromethylalkenes

Chuan Zhu et al.

Summary: Transition-metal-catalyzed difunctionalization of olefins is a powerful method to access complex molecules from bulk chemicals. In this study, a hydroalkylation reaction of trifluoromethylalkenes with alkyl halides under nickel catalysis was developed, leading to the efficient construction of 1,1,1-trifluoropropane derivatives. The commonly observed beta-fluoride elimination pathway was suppressed by using a competent proton donor, enabling the use of substrates featuring fluoroalkyl substituents.

ACS CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Defluorinative Asymmetric Cyclization of Fluoroalkyl-Substituted 1,6-Enynes for the Synthesis of Seletracetam

Kuai Wang et al.

Summary: The introduction of fluorine-containing groups into organic molecules can significantly affect their physical and chemical properties and has been widely used in drug discovery and development. In this study, a nickel-catalyzed asymmetric cyclization reaction was described, which enables the efficient synthesis of synthetically attractive 4-fluorovinyl-substituted 2-pyrrolidones. This protocol shows high chemo-, regio-, and enantioselectivities and can be utilized in the synthesis of the antiepileptic drug Seletracetam.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

Light-Induced Iron-Catalyzed Trifluoromethylative Thiolation of Alkenes

Xiaonan Zhang et al.

Summary: A series of novel trifluoromethylative thiolation reactions were successfully achieved using visible light and iron salts as catalysts, resulting in moderate to good yields of 1,2-bis(trifluoromethylated) compounds. These reactions proceed in an atom-economical manner with a broad substrate scope, and are tolerant of biologically active chemicals, making them potentially useful for late-stage modification in pharmaceutical discovery. Additionally, the desired products were successfully synthesized on a gram scale using flow-setup synthesis, demonstrating the synthetic power of these reactions in industrial applications.

ORGANIC LETTERS (2022)

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Article Chemistry, Physical

Reductive quenching-initiated catalyst-controlled divergent alkylation of α-CF3-olefins

Yunxiao Zhang et al.

Summary: This research demonstrates a visible-light-induced photo-catalyst strategy for preparing both gem-difluoroalkenes and trifluoromethyl alkanes from alpha-CF3-olefins. The selectivity of the reactions depends on the choice of catalyst rather than the modification of substrate structures.

CHEM CATALYSIS (2022)

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Article Chemistry, Organic

Fe-catalyzed hydroxytrifluoromethylation of α-(trifluoromethyl)styrenes with CF3SO2Na: facile access to α,β-bistrifluoromethyl tertiary alcohols

Pai Zheng et al.

Summary: A mild and practical Fe-catalyzed hydroxytrifluoromethylation of alpha-(trifluoromethyl)styrenes with CF3SO2Na in the presence of K2S2O8 and air has been developed. The reaction proceeds efficiently at room temperature without beta-fluoride elimination, resulting in good to excellent yields of alpha, beta-bistrifluoromethyl tertiary alcohols.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Selective approach to N-substituted tertiary 2-pyridones

Yu Wang et al.

Summary: Regio- and enantioselective amination of readily available vinyl cyclic carbonates with ambivalent 2-hydroxypyridines has been achieved using a Pd(0)/DACH-naphthyl catalyst system. The reaction proceeds under simple conditions, providing access to chiral N-substituted 2-pyridones that bear elusive tertiary carbon centers. This catalytic method overcomes a significant drawback previously associated with transition metal-catalyzed allylic substitution procedures.

NEW JOURNAL OF CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Et3N-Catalyzed Cycloaddition Reactions of α-(Trifluoromethyl)styrenes with 2,2,2-Trifluorodiazoethane to Access Bis(trifluoromethyl)-Substituted Pyrazolines

Chunmei Li et al.

Summary: A novel and practical method for the synthesis of 3,5-bis(trifluoromethyl)-4,5-dihydro-1H-pyrazoles using [3+2] cycloaddition reactions has been developed, achieving good to excellent yields and exhibiting a broad substrate scope with tolerance to various functional groups.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Organic

Ruthenium-Catalyzed Chemoselective N-H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides

Xiaofeng Liu et al.

Summary: A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, providing N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to this unprecedented reaction is the use of CpRu(PPh3)(2)Cl as the catalyst and sulfoxonium ylides as the alkylation reagents, which can also be applied to 7-azaindoles with slight variations in reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents for good selectivity in N-alkylation of 2-pyridones.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Two C(sp3)-F Bond Activation in a CF3 Group: ipso-Defluorinative Amination Triggered 1,3-Diamination of (Trifluoromethyl)alkenes with Indoles, Carbazoles, Pyrroles, and Sulfonamides

Hao Zeng et al.

Summary: A novel strategy for cleaving two C(sp(3))-F bonds in a CF3 group has been reported. This strategy involves ipso-defluorinative amination of (trifluoromethyl)alkenes with various nitrogen-containing compounds to yield acyclic 1,3-diamine products with monofluoroalkene moiety in high yields with good to excellent selectivities. Preliminary mechanistic studies suggest a unique sequential ipso-/gamma-selective defluorinative amination pathway in this transformation.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Direct Synthesis of N-Difluoromethyl-2-pyridones from Pyridines

Sen Zhou et al.

Summary: A novel method for synthesizing N-difluoromethyl-2-pyridones from readily available pyridines has been described, utilizing mild reaction conditions and identifying N-difluoromethylpyridinium salts as key intermediates in the conversion process.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Copper-Catalyzed Regioselective Coupling of Tosylhydrazones and 2-Pyridones: A Strategy for the Production of N-Alkylated Compounds

Ye-bin Wu et al.

Summary: The highly regioselective N-alkylation reaction of 2-pyridones with bulky secondary alkyl groups was achieved through hydrazone chemistry using a copper-catalyzed coupling reaction with tosylhydrazones.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Dual Roles of TBHP-Enabled Regioselective Hydroetherification of (Trifluoromethyl)alkenes with Boronic Acids: Access to α-Trifluoromethyl β-Aryloxy Tertiary Alcohols

Hengyuan Li et al.

Summary: The study reports a three-starting materials four-component reaction of (trifluoromethyl)alkenes, TBHP, and boronic acids, which delivers various useful alpha-trifluoromethyl-beta-aryloxy tertiary alcohols in high yields and in an exclusively regioselective hydroetherification manner. TBHP serves multiple roles in this reaction, functioning as both the oxidant and nucleophile, as well as the O-source of the products.

SYNTHESIS-STUTTGART (2021)

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Article Multidisciplinary Sciences

Chemoselective catalytic hydrodefluorination of trifluoromethylalkenes towards mono-/gem-di-fluoroalkenes under metal-free conditions

Jingjing Zhang et al.

Summary: The diazaphospholene-catalyzed hydrodefluorination can selectively construct gem-difluoroalkenes and terminal monofluoroalkenes, showing good group compatibility and almost quantitative yields.

NATURE COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary

Recent advances in chemistry and pharmacological aspects of 2-pyridone scaffolds

Mostafa M. K. Amer et al.

Summary: The chemistry and applications of 2-pyridone structures have attracted attention recently. These structures exhibit diverse biological activities, and can be used for synthesizing various compounds and drug precursors. Studying substituted 2-pyridones can provide insights for future research on structure-activity relationships and mechanisms of action.

JOURNAL OF SAUDI CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Synthesis of CF3-Containing Linear Nitriles from α-(Trifluoromethyl)styrenes

Sixue Xu et al.

Summary: Four unprecedented base-catalyzed/mediated nucleophilic additions of TMSCN to alpha-(trifluoromethyl)styrenes and 2-trifluoromethyl enynes have been developed. The reaction proceeds smoothly at room temperature under mild and transition-metal-free conditions, affording the corresponding CF3-containing alkyl, alkynyl, and butadienyl nitriles in a highly regioselective manner with moderate to excellent yields.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Chemoselective N- and O-Difluoromethylation of 2-Pyridones, Isoquinolinones, and Quinolinones with TMSCF2Br

Ziyue Zhu et al.

Summary: A straightforward protocol for direct difluoromethylation of specific organic compounds is presented, showing tolerance towards various functional groups. The selectivity of the reaction can be modulated by simple variations in reaction conditions. Gram-scale reactions for preparing difluoromethyl compounds are demonstrated.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Ruthenium (VIII) Catalysed Dearomative Pyridyl C-X Activation: Direct Synthesis of N- Alkyl-2-pyridones

Biswajit Das et al.

Summary: This study describes an efficient synthetic strategy using pyridyl C-X activation to generate N-alkyl-2-pyridones from N-alkyl-2-halopyridinium salts. The strategy involves an in-situ generation of Ru(VIII) for catalytic dearomative synthesis of pyridones, which can be further reduced to N-alkyl-2-piperidones. A plausible mechanism is proposed based on controlled reactions.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Photoredox relay-catalyzed gem-difluoroallylation of alkyl iodides

Yuanqiang Guo et al.

Summary: A new example of relay catalysis using a combination of Mn-2(CO)(10) and an iridium-based photocatalyst has been reported. The Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, transforming alkyl iodides into gem-difluoroalkenes with good functional group tolerance. This convenient method is suitable for late-stage modification of multifunctional complex molecules.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Organic

Visible-light-promoted selective O-alkylation of 2-pyridones with α-aryldiazoacetates

Jingya Yang et al.

Summary: The visible-light-promoted O-H insertion reaction between 2-pyridones and alpha-aryldiazoacetates proceeds smoothly under mild and catalyst-free conditions, leading to a wide scope of O-alkylated 2-pyridones with perfect selectivity and good functional group tolerance, likely attributed to a photoinduced radical process.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Organic

Photocatalyst-Free Singlet Oxygen-Induced Oxygenation: A Strategy for the Preparation of 5-Cyano-2-pyridones Driven by Blue-Light Irradiation

Mengmeng Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Dearomative Migratory Rearrangement of 2-Oxypyridines Enabled by α-Imino Rhodium Carbene

Guangyang Xu et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Organic

Pyridones - Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds

Jacek G. Sosnicki et al.

SYNTHESIS-STUTTGART (2019)

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Article Chemistry, Physical

Copper-Catalyzed Carboxylation of C-F Bonds with CO2

Si-Shun Yan et al.

ACS CATALYSIS (2019)

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Article Chemistry, Applied

Organocatalyzed Enantioselective Michael Addition of 2-Hydroxypyridines and α,β-Unsaturated 1,4-Dicarbonyl Compounds

Yu-Chun Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Access to N-Substituted 2-Pyridones by Catalytic Intermolecular Dearomatization and 1,4-Acyl Transfer

Guangyang Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Medicinal

The Journey of HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) from Lab to Clinic

Vigneshwaran Namasivayam et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Pd-Catalyzed regio- and enantioselective allylic substitution with 2-pyridones

Sardaraz Khan et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Photocatalytic hydroacylation of trifluoromethyl alkenes

Pei Fan et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst

Atul K. Godha et al.

NEW JOURNAL OF CHEMISTRY (2019)

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Article Chemistry, Organic

Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides

Bin Feng et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Synthesis of N-alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives

Gang Hu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Review Chemistry, Multidisciplinary

A lesson for site-selective C-H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls

Koji Hirano et al.

CHEMICAL SCIENCE (2018)

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Article Chemistry, Applied

Catalytic O- to N-Alkyl Migratory Rearrangement: Transition Metal-Free Direct and Tandem Routes to N-Alkylated Pyridones and Benzothiazolones

Abhishek Kumar Mishra et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Medicinal

Idiopathic Pulmonary Fibrosis: Current Status, Recent Progress, and Emerging Targets

Yi-Min Liu et al.

JOURNAL OF MEDICINAL CHEMISTRY (2017)

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Article Chemistry, Organic

Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones

Jacob C. Timmerman et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Applied

Development of a Practical Synthesis of a Peripherally Selective Noradrenaline Reuptake Inhibitor Possessing a Chiral 6,7-trans-Disubstituted-1,4-oxazepane as a Scaffold

Kazuhisa Ishimoto et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2017)

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Article Chemistry, Organic

N-alkylation of 2-pyridone derivatives via palladium(II)-catalyzed directed alkene hydroamination

John A. Gurak et al.

TETRAHEDRON (2017)

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Article Chemistry, Organic

Synthesis of N-Alkenyl 2-Pyridonyl Ethers via a Au(I)-Catalyzed Rearrangement of 2-Propargyloxypyridines

Evan O. Romero et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Applied

Gold-Catalyzed Intermolecular anti-Markovnikov Hydroamination of Methylenecyclopropanes with 2-Pyridones

Jacob C. Timmerman et al.

ADVANCED SYNTHESIS & CATALYSIS (2015)

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Article Chemistry, Organic

Mild and Regioselective N-Alkylation of 2-Pyridones in Water

Xin Hao et al.

ORGANIC LETTERS (2015)

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Article Chemistry, Multidisciplinary

Highly Regio- and Enantioselective Synthesis of N-Substituted 2-Pyridones: Iridium-Catalyzed Intermolecular Asymmetric Allylic Amination

Xiao Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective Addition of 2-Pyridones to Terminal Allenes

Changkun Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Article Biochemistry & Molecular Biology

Ricinine: A pyridone alkaloid from Ricinus communis that activates the Wnt signaling pathway through casein kinase 1α

Kensuke Ohishi et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2014)

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Article Chemistry, Medicinal

Discovery of 1-Buty1-3-chloro-4-(4-pheny1-1-piperidiny1)(1H)-pyridone (JNJ-40411813): A Novel Positive Allosteric Modulator of the Metabotropic Glutamate 2 Receptor

Jose Maria Cid et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

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Article Chemistry, Organic

Ir(I)-Catalyzed Synthesis of N-Substituted Pyridones from 2-Alkoxypyridines via C-O Bond Cleavage

Shiguang Pan et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Medicinal

Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (Perampanel): A Novel, Noncompetitive α-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic Acid (AMPA) Receptor Antagonist

Shigeki Hibi et al.

JOURNAL OF MEDICINAL CHEMISTRY (2012)

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Article Chemistry, Organic

Preparation of N-Alkyl 2-Pyridones via a Lithium Iodide Promoted O- to N-Alkyl Migration: Scope and Mechanism

Sarah Z. Tasker et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

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Article Chemistry, Multidisciplinary

Ru-catalyzed activation of sp3 C-O bonds: O- to N-alkyl migratory rearrangement in pyridines and related heterocycles

Charles S. Yeung et al.

CHEMICAL SCIENCE (2011)

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Article Chemistry, Multidisciplinary

Ambident Reactivities of Pyridone Anions

Martin Breugst et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Medicinal

Pyridones as glucokinase activators: Identification of a unique metabolic liability of the 4-sulfonyl-2-pyridone heterocycle

Jeffrey A. Pfefferkorn et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2009)

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Article Chemistry, Organic

Synthesis of substituted N-benzyl pyridones via an O- to N-alkyl migration

Erica L. Lanni et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

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Highly Regioselective Synthesis of N-β-trifluoromethyl 2-pyridones via anti-Markovnikov Hydroamination of α-(trifluoromethyl)styrenes with 2-pyridones

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