Cu(II) Catalyzed Imine C–H Functionalization Leading to Synthesis of 2,5-Substituted 1,3,4-Oxadiazoles

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C–H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-cat...

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Published inOrganic letters Vol. 13; no. 22; pp. 5976 - 5979
Main Authors Guin, Srimanta, Ghosh, Tuhin, Rout, Saroj Kumar, Banerjee, Arghya, Patel, Bhisma K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.11.2011
Amer Chemical Soc
Subjects
Carbon - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Hydrogen - chemistry
Imines - chemistry
Molecular Structure
Oxadiazoles - chemical synthesis
Oxidation-Reduction
Physical Sciences
Science & Technology
LIGHT-EMITTING-DIODES
DIRECT ARYLATION
DIRECT AMINATION
ONE-POT SYNTHESIS
2-ARYLBENZOXAZOLES
BENZODIAZEPINE
BENZOXAZOLES
N BOND FORMATION
OPTIMIZATION
OXADIAZOLES
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Summary:A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C–H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C–H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol202409r