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research article
Zinc Bromide Promoted Coupling of Isonitriles with Carboxylic Acids To Form 2,4,5-Trisubstituted Oxazoles
Deviant behavior: In a deviation from “normal” reactivity, isocyanides underwent co-trimerization with carboxylic acids in the presence of ZnBr2 to smoothly provide oxazoles (see scheme). The reaction is thought to occur by initial nucleophilic addition of the carboxylic acid to a ligated isonitrile molecule, followed by a sequence involving double migratory insertion, metal-salt elimination, acyl migration, cyclization, and dealkylation.
Type
research article
Web of Science ID
WOS:000325157600044
Author(s)
Date Issued
2013
Publisher
Published in
Volume
52
Issue
41
Start page
10878
End page
10882
Peer reviewed
REVIEWED
Written at
EPFL
EPFL units
Available on Infoscience
October 2, 2013
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