Preparation of Primary Amides from Functionalized Organozinc Halides

Organozinc halides, which are prepared either by direct zinc insertion or halogen−magnesium exchange and subsequent transmetalation with ZnCl2, react smoothly with commercially available trichloroacetyl isocyanate to give, after hydrolysis, the corresponding primary amides. This method is compatible...

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Bibliographic Details
Published in:Organic letters 2010-08, Vol.12 (16), p.3648-3650
Main Authors: Schade, Matthias A, Manolikakes, Georg, Knochel, Paul
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Amides - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Zinc - chemistry
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Summary:Organozinc halides, which are prepared either by direct zinc insertion or halogen−magnesium exchange and subsequent transmetalation with ZnCl2, react smoothly with commercially available trichloroacetyl isocyanate to give, after hydrolysis, the corresponding primary amides. This method is compatible with a variety of functional groups such as an ester or a cyano group. Also heterocyclic-, alkenyl, and acetylenic zinc reagents are converted to the corresponding primary amides under these conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101469f