α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation

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Abstract: Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α‐arylated and α‐oxyaminated acetophenones under metal‐free conditions in moderate to excellent yields and enables extension to the synthesis of arylated morpholines via generation of vinylsulfonium salts. Computational investigations confirmed the transient existence of intermediates derived from vinyl triflates and the role of the oxygen atoms at the para position of aromatic ring in facilitating their stabilisation.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation ; volume:59 ; number:47 ; year:2020 ; pages:20935-20939 ; extent:5
Angewandte Chemie / International edition. International edition ; 59, Heft 47 (2020), 20935-20939 (gesamt 5)

Creator: Zawodny, Wojciech
Teskey, Christopher J.
Mishevska, Magdalena
Völkl, Martin
Maryasin, Boris
González, Leticia
Maulide, Nuno

DOI: 10.1002/anie.202006398

URN: urn:nbn:de:101:1-2022061313382451999197

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:22 AM CEST

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Associated

Zawodny, Wojciech
Teskey, Christopher J.
Mishevska, Magdalena
Völkl, Martin
Maryasin, Boris
González, Leticia
Maulide, Nuno

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Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

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α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation

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Other Objects (12)

Quantification of electrophilic reactivities of ketones and heteroallenes

Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions

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Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

Ligand-Constraint-Induced Peroxide Activation for Electrophilic Reactivity

Electrophilic ring bond activation of 2H-Azaphosphirene complexes

Two Directing Groups Used for Metal Catalysed Meta ‐C−H Functionalisation Only Effect Ortho Electrophilic C−H Borylation

Organic functionalisation and post-functionalisation of polynuclear vanadium compounds

Metal-Free Oxidative C–C Bond Cleavage of Ketones Promoted by Biomass-Derived Carbons

Metal‐Free Photochemical Olefin Isomerization of Unsaturated Ketones via 1,5‐Hydrogen Atom Transfer

Enamide Synthesis from Amides Using Tf2O for Electrophilic Activation

Quantification of electrophilic reactivities of ketones and heteroallenes

Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions

Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions

Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

Ligand-Constraint-Induced Peroxide Activation for Electrophilic Reactivity

Electrophilic ring bond activation of 2H-Azaphosphirene complexes

Two Directing Groups Used for Metal Catalysed Meta ‐C−H Functionalisation Only Effect Ortho Electrophilic C−H Borylation

Organic functionalisation and post-functionalisation of polynuclear vanadium compounds

Metal-Free Oxidative C–C Bond Cleavage of Ketones Promoted by Biomass-Derived Carbons

Metal‐Free Photochemical Olefin Isomerization of Unsaturated Ketones via 1,5‐Hydrogen Atom Transfer

Enamide Synthesis from Amides Using Tf2O for Electrophilic Activation

Quantification of electrophilic reactivities of ketones and heteroallenes

Electrophilic Vinylation of Thiols under Mild and Transition Metal‐Free Conditions

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Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

Ligand‐Constraint‐Induced Peroxide Activation for Electrophilic Reactivity

Ligand-Constraint-Induced Peroxide Activation for Electrophilic Reactivity

Electrophilic ring bond activation of 2H-Azaphosphirene complexes

Two Directing Groups Used for Metal Catalysed Meta ‐C−H Functionalisation Only Effect Ortho Electrophilic C−H Borylation

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