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 ZnCl(2), 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.
Schade
Matthias A
MA
Department Chemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 München, Germany.
Manolikakes
Georg
G
Knochel
Paul
P
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D015032:Zinc / Q000737:chemistry*
D000577:Amides; D006846:Hydrocarbons, Halogenated; D015032:Zinc