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  4. Zinc Bromide Promoted Coupling of Isonitriles with Carboxylic Acids To Form 2,4,5-Trisubstituted Oxazoles
 
research article

Zinc Bromide Promoted Coupling of Isonitriles with Carboxylic Acids To Form 2,4,5-Trisubstituted Oxazoles

Odabachian, Yann  
•
Tong, Shuo  
•
Wang, Qian  
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2013
Angewandte Chemie International Edition

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.

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Type
research article
DOI
10.1002/anie.201305506
Web of Science ID

WOS:000325157600044

Author(s)
Odabachian, Yann  
Tong, Shuo  
Wang, Qian  
Wang, Mei-Xiang
Zhu, Jieping  
Date Issued

2013

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

52

Issue

41

Start page

10878

End page

10882

Subjects

domino reactions

•

isocyanides

•

Lewis acids

•

oxazoles

•

rearrangement

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
October 2, 2013
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/96050
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