Photoredox catalyzed C-H trifluoroethylamination of heteroarenes

Article Chemistry, Multidisciplinary

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Yao Ouyang et al.

Summary: The study introduces a novel electrochemical reaction method for the direct trifluoromethoxylation of aromatics, providing a valuable structural motif for drug discovery.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed N-Arylation of Fluoroalkylamines

Ryan T. McGuire et al.

Summary: The report presents the first Ni-catalyzed N-arylation of beta-fluoroalkylamines with broad scope. The use of a stable pre-catalyst allows for reactions to be conducted at room temperature or using a commercially available dual-base system, providing a mild protocol with broad substrate scope and enantioselective transformations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Nucleophilic and Radical Heptafluoroisopropoxylation with Redox-Active Reagents

Chao-Lai Tong et al.

Summary: Efficient heptafluoroisopropoxylation reactions were achieved through the invention of a series of redox-active N-OCF(CF3)(2) reagents. Various substrates can undergo direct heptafluoroisopropoxylation to yield products in moderate to excellent yields.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Iron porphyrin-catalyzed N-trifluoroethylation of anilines with 2,2,2-trifluoroethylamine hydrochloride in aqueous solution

Shuang Ren et al.

Summary: An iron porphyrin-catalyzed N-trifluoroethylation of anilines has been developed using 2,2,2-trifluoroethylamine hydrochloride as the fluorine source. This one-pot N-H insertion reaction is achieved through cascade diazotization/N-trifluoroethylation reactions, providing a range of N-trifluoroethylated anilines in good yields with readily available primary amines and secondary anilines as starting materials.

RSC ADVANCES (2021)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Regioselective Arylation of Unprotected Allylamines

Vinod G. Landge et al.

Summary: The translation discusses the challenges of palladium-catalyzed organometallic transformations of free amines and the importance of accessing free amine products. It also highlights the significance of the 3,3-diarylallylamine motif and the development of a catalytic approach for their synthesis. The method allows for mild conditions, broad substrate scope, and direct diarylation of terminal allylamine substrates.

JACS AU (2021)

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Review Chemistry, Multidisciplinary

When Light Meets Nitrogen-Centered Radicals: From Reagents to Catalysts

Xiao-Ye Yu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

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Article Chemistry, Medicinal

Metabolic and Pharmaceutical Aspects of Fluorinated Compounds

Benjamin M. Johnson et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

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Article Chemistry, Organic

Selective N7 Alkylation of 7-Azaindazoles

Zhiyu Lei et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Physical

Enantioselective Synthesis of Fluoroalkyl-Substituted syn-Diamines by the Asymmetric gem-Difunctionalization of 2,2,2-Trifluorodiazoethane

Jiuling Li et al.

ACS CATALYSIS (2020)

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Review Chemistry, Multidisciplinary

Contribution of Organofluorine Compounds to Pharmaceuticals

Munenori Inoue et al.

ACS OMEGA (2020)

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Article Chemistry, Applied

DirectN-Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition-Metal-Free Catalysis

Chunlei Lu et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Review Chemistry, Multidisciplinary

2,2,2-Trifluorodiazoethane (CF3CHN2): A Long Journey since 1943

Pavel K. Mykhailiuk

CHEMICAL REVIEWS (2020)

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Article Chemistry, Organic

Silver-Catalyzed C-H Aryloxydifluoromethylation and Arylthiodifluoromethylation of Heteroarenes

Xiao-Lei Zhu et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

A Single-Step Synthesis of Azetidine-3-amines

Brian J. Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Multidisciplinary Sciences

Current Contributions of Organofluorine Compounds to the Agrochemical Industry

Yuta Ogawa et al.

ISCIENCE (2020)

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Article Chemistry, Multidisciplinary

Copper-catalyzed chemoselective C-H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

Hai-Yan Su et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Chemistry, Multidisciplinary

The Fluorination of C-H Bonds: Developments and Perspectives

Robert Szpera et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

Saikat Maiti et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Regio- and Enantioselective Allylic Amination

Samir Ghorai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Applied

B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane

Yixiao Pan et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Overcoming inaccessibility of fluorinated imines - synthesis of functionalized amines from readily available fluoroacetamides

Pawel J. Czerwinski et al.

CHEMICAL COMMUNICATIONS (2019)

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Review Chemistry, Multidisciplinary

Chemistry With N-Centered Radicals Generated by Single-Electron Transfer-Oxidation Using Photoredox Catalysis

Heng Jiang et al.

CCS CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent

Yao Ouyang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Multidisciplinary

Hydroxylamine Derivatives as Nitrogen-Radical Precursors in Visible-Light Photochemistry

Jacob Davies et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Article Chemistry, Medicinal

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design

Nicholas A. Meanwell

JOURNAL OF MEDICINAL CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling

Joseph M. Dennis et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Direct and Regioselective C-H Oxidative Difluoromethylation of Heteroarenes

Sheng-Qing Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Organic

Transition-Metal-Free Decarboxylation of 3,3,3-Trifluoro-2,2-dimethylpropanoic Acid for the Preparation of C(CF3)Me-2-Containing Heteroarenes

Shuai Liu et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Organic

Reductive N-alkylation of primary and secondary amines using carboxylic acids and borazane under mild conditions

Yahui Wei et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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Article Chemistry, Multidisciplinary

One-Pot 1,1-Dihydrofluoroalkylation of Amines Using Sulfuryl Fluoride

Maxim Epifanov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Review Chemistry, Multidisciplinary

Palladium-Catalyzed Transformations of Alkyl C-H Bonds

Jian He et al.

CHEMICAL REVIEWS (2017)

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Article Multidisciplinary Sciences

A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid

Keith G. Andrews et al.

NATURE COMMUNICATIONS (2017)

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Article Chemistry, Physical

Photochemical Generation of Nitrogen-Centered Amidyl, Hydrazonyl, and Imidyl Radicals: Methodology Developments and Catalytic Applications

Markus D. Karkas

ACS CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Transition metal-free N-fluoroalkylation of amines using cyanurate activated fluoroalcohols

Fatemeh Haghighi et al.

CHEMICAL COMMUNICATIONS (2017)

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Review Chemistry, Multidisciplinary

C-H Functionalization of Azines

Kei Murakami et al.

CHEMICAL REVIEWS (2017)

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Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed C-H Amination: Scope, Mechanism, and Applications

Yoonsu Park et al.

CHEMICAL REVIEWS (2017)

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Review Chemistry, Multidisciplinary

Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes

Yudong Yang et al.

CHEMICAL REVIEWS (2017)

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Article Chemistry, Organic

Direct, Regioselective N-Alkylation of 1,3-Azoles

Shuai Chen et al.

ORGANIC LETTERS (2016)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes

Stephen Hyde et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Review Chemistry, Multidisciplinary

Visible light photoredox-controlled reactions of N-radicals and radical ions

Jia-Rong Chen et al.

CHEMICAL SOCIETY REVIEWS (2016)

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Article Chemistry, Organic

Photoredox Catalysis Mediated Application of Methyl Fluorosulfonyldifluoroacetate as the CF2CO2R Radical Source

Wei Yu et al.

ORGANIC LETTERS (2016)

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Article Multidisciplinary Sciences

Aryl amination using ligand-free Ni(II) salts and photoredox catalysis

Emily B. Corcoran et al.

SCIENCE (2016)

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Article Chemistry, Multidisciplinary

Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids

Ming-Chen Fu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Silver(I)-Catalyzed N-Trifluoroethylation of Anilines and O-Trifluoroethylation of Amides with 2,2,2-Trifluorodiazoethane

Haiqing Luo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Arylation of Fluoroalkylamines

Andrew T. Brusoe et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Multidisciplinary

Direct Catalytic N-Alkylation of Amines with Carboxylic Acids

Ivan Sorribes et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Organic

Efficient synthesis of mibefradil analogues: an insight into in vitro stability

Ji Eun Lee et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

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Article Chemistry, Organic

Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C-H Bonds via Nondirected Oxidative C(sp3)-H Activation

Chao Chen et al.

ORGANIC LETTERS (2014)

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Review Chemistry, Multidisciplinary

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

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Article Chemistry, Organic

Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3,5-Dichloropyrazines

Stephanie Scales et al.

ORGANIC LETTERS (2013)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes

Lingling Chu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

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Article Chemistry, Medicinal

New Fluorinated 1,2,4-Benzothiadiazine 1,1-Dioxides: Discovery of an Orally Active Cognitive Enhancer Acting through Potentiation of the 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic Acid Receptors

Pierre Francotte et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

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Article Chemistry, Applied

Multi-kiloscale enantioselective synthesis of a vitronectin receptor antagonist

MD Wallace et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2004)

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Article Chemistry, Organic

Convenient synthesis of 2-benzazepines via radical cyclization

A Kamimura et al.

JOURNAL OF ORGANIC CHEMISTRY (2003)

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Photoredox catalyzed C-H trifluoroethylamination of heteroarenes

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