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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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2011-07, Vol.7 (1), p.997-1002
Main Authors: Le Gall, Erwan, Pignon, Antoine, Martens, Thierry
Format: Article
Language:English
Subjects:
acyliminium
amides
carbamates
Chemistry
Letter
multicomponent reactions
organozinc reagents
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Summary: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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.7.112