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Literature DB >> 28590518

Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation.

Maximilian A Ganiek¹, Matthias R Becker¹, Guillaume Berionni¹, Hendrik Zipse¹, Paul Knochel¹.

Abstract

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.

Entities: Chemical

Keywords: Barbier reaction; acidity; amidation; flow chemistry; lithiation

Year: 2017 PMID： 28590518 DOI： 10.1002/chem.201702593

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

6 in total

1. (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.

Authors: Johannes H Harenberg; Niels Weidmann; Alexander J Wiegand; Carla A Hoefer; Rajasekar Reddy Annapureddy; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2021-05-03 Impact factor: 15.336

2. An organophotocatalytic late-stage N-CH₃ oxidation of trialkylamines to N-formamides with O₂ in continuous flow.

Authors: Mark John P Mandigma; Jonas Žurauskas; Callum I MacGregor; Lee J Edwards; Ahmed Shahin; Ludwig d'Heureuse; Philip Yip; David J S Birch; Thomas Gruber; Jörg Heilmann; Matthew P John; Joshua P Barham
Journal: Chem Sci Date: 2021-12-28 Impact factor: 9.825

Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation.

1. (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.

2. An organophotocatalytic late-stage N-CH₃ oxidation of trialkylamines to N-formamides with O₂ in continuous flow.

3. Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

4. Preparation of Functionalized Amides Using Dicarbamoylzincs.

5. The Concept of Chemical Generators: On-Site On-Demand Production of Hazardous Reagents in Continuous Flow.

6. Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates.

Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation.

1. (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.

2. An organophotocatalytic late-stage N-CH3 oxidation of trialkylamines to N-formamides with O2 in continuous flow.

3. Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

4. Preparation of Functionalized Amides Using Dicarbamoylzincs.

5. The Concept of Chemical Generators: On-Site On-Demand Production of Hazardous Reagents in Continuous Flow.

6. Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates.

2. An organophotocatalytic late-stage N-CH₃ oxidation of trialkylamines to N-formamides with O₂ in continuous flow.