New Reactivity of Oxaziridine: Pd(II)-Catalyzed Aromatic C–H Ethoxycarbonylation via C–C Bond Cleavage

A novel Pd(II)-catalyzed aromatic C–H ethoxycarbonylation with oxaziridine involving C–C bond cleavage is described. Various aromatic 2-phenylpyridines and related compounds as well as aryl ureas can be effectively ethoxycarbonylated. A catalytic cycle involving Pd(II) and Pd(IV) is proposed.

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 19; pp. 5244 - 5247
Main Authors Peng, Xingao, Zhu, Yingguang, Ramirez, Thomas A, Zhao, Baoguo, Shi, Yian
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.10.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PD-CATALYZED DIAMINATION
PALLADIUM
ACTIVATION
COUPLING REACTIONS
CU(I)-CATALYZED REGIOSELECTIVE DIAMINATION
CONJUGATED DIENES
ARYL
CARBOXYLATION
CATALYZED ASYMMETRIC EPOXIDATION
TERMINAL OLEFINS
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Summary:A novel Pd(II)-catalyzed aromatic C–H ethoxycarbonylation with oxaziridine involving C–C bond cleavage is described. Various aromatic 2-phenylpyridines and related compounds as well as aryl ureas can be effectively ethoxycarbonylated. A catalytic cycle involving Pd(II) and Pd(IV) is proposed.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol2021252