Rhodium(I)-Catalyzed-Coupling Cyclization of C=0 Bonds with α-Diazoketones

An unprecedented intermolecular nucleophilic attack of C=X bonds (X = 0 and 5) on the rhodium(I)-carbenes has been developed. This transformation allows for the coupling-cyclization of aroylamides with alpha-diazoketones and provides concise access to 2,4,5-trisubstituted 1,3-oxazoles and 1,3-thiazo...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 13; pp. 3980 - 3983
Main Authors Chen, Ziyang, Hu, Xinwei, Huang, Junmin, Zeng, Wei
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 06.07.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ACTIVATION
ARYLDIAZOACETATES
CARBENE INSERTION
REGIOSELECTIVE SYNTHESIS
CYCLOPROPANATION
DIAZO-COMPOUNDS
C-H FUNCTIONALIZATION
STRAIGHTFORWARD ACCESS
DIAZOCARBONYL COMPOUNDS
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Summary:An unprecedented intermolecular nucleophilic attack of C=X bonds (X = 0 and 5) on the rhodium(I)-carbenes has been developed. This transformation allows for the coupling-cyclization of aroylamides with alpha-diazoketones and provides concise access to 2,4,5-trisubstituted 1,3-oxazoles and 1,3-thiazoles with a broad tolerance of functional groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01541