A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation by the carbonyl-containing electrophile and t...

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Main Authors: Erwan Le Gall, Antoine Pignon, Thierry Martens
Format: Article
Language:English
Published: Beilstein-Institut 2011-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.7.112
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author Erwan Le Gall
Antoine Pignon
Thierry Martens
author_facet Erwan Le Gall
Antoine Pignon
Thierry Martens
author_sort Erwan Le Gall
collection DOAJ
description A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation by the carbonyl-containing electrophile and the trapping of the acyliminium by an organozinc reagent. Most steps are conducted concomitantly to render the procedure as practical and straightforward as possible. Therefore, the whole experimental protocol takes less than two hours.
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spelling doaj.art-3d5f437dac834b6d932c5434acca09ad2022-12-21T20:00:38ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-07-0171997100210.3762/bjoc.7.1121860-5397-7-112A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformatesErwan Le Gall0Antoine Pignon1Thierry Martens2Électrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS - Université Paris-Est Créteil, 2-8 rue Henri Dunant, 94320 Thiais, FranceÉlectrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS - Université Paris-Est Créteil, 2-8 rue Henri Dunant, 94320 Thiais, FranceÉlectrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS - Université Paris-Est Créteil, 2-8 rue Henri Dunant, 94320 Thiais, FranceA practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation by the carbonyl-containing electrophile and the trapping of the acyliminium by an organozinc reagent. Most steps are conducted concomitantly to render the procedure as practical and straightforward as possible. Therefore, the whole experimental protocol takes less than two hours.https://doi.org/10.3762/bjoc.7.112acyliminiumamidescarbamatesmulticomponent reactionsorganozinc reagents
spellingShingle Erwan Le Gall
Antoine Pignon
Thierry Martens
A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
Beilstein Journal of Organic Chemistry
acyliminium
amides
carbamates
multicomponent reactions
organozinc reagents
title A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
title_full A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
title_fullStr A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
title_full_unstemmed A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
title_short A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates
title_sort practical route to tertiary diarylmethylamides or carbamates from imines organozinc reagents and acyl chlorides or chloroformates
topic acyliminium
amides
carbamates
multicomponent reactions
organozinc reagents
url https://doi.org/10.3762/bjoc.7.112
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