Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation

Maximilian A. Ganiek, Matthias R. Becker, Guillaume Berionni, Hendrik Zipse, Paul Knochel

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

An ambient temperature continuous flow method for nucleophilic amidation and thioamidation is described. Deprotonation of formamides by lithium diisopropylamine (LDA) affords carbamoyllithium intermediates that are quenched in situ with various electrophiles such as ketones, allyl bromides, Weinreb and morpholino amides. The nature of the reactive lithium intermediates and the thermodynamics of the metalation were further investigated by ab initio calculations and kinetic experiments.

langueAnglais
Pages10280-10284
Nombre de pages5
journalChemistry - A European Journal
Volume23
Numéro43
Les DOIs
étatPublié - 1 août 2017
Modification externeOui

Empreinte digitale

Lithium
Formamides
Morpholinos
Deprotonation
Ketones
Amides
Thermodynamics
Kinetics
Experiments
Temperature
diisopropylamine
allyl bromide

mots-clés

    Citer ceci

    Ganiek, Maximilian A. ; Becker, Matthias R. ; Berionni, Guillaume ; Zipse, Hendrik ; Knochel, Paul. / Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation. Dans: Chemistry - A European Journal. 2017 ; Vol 23, Numéro 43. p. 10280-10284
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    Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation. / Ganiek, Maximilian A.; Becker, Matthias R.; Berionni, Guillaume; Zipse, Hendrik; Knochel, Paul.

    Dans: Chemistry - A European Journal, Vol 23, Numéro 43, 01.08.2017, p. 10280-10284.

    Résultats de recherche: Contribution à un journal/une revueArticle

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