Heteroarylation of Azine N-Oxides

Azine N-oxides undergo highly regioselective metalation with TMPZnCl·LiCl under mild conditions. A palladium-catalyzed Negishi cross-coupling reaction of the resulting organozinc species with heteroaromatic bromides provides heterobiaryls specifically oxidized at one nitrogen position in up to 95% y...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 3; pp. 862 - 865
Main Authors Gosselin, Francis, Savage, Scott J, Blaquiere, Nicole, Staben, Steven T
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.02.2012
Amer Chemical Soc
Subjects
Bromides - chemistry
Catalysis
Chemistry
Chemistry, Organic
Heterocyclic Compounds - chemistry
Molecular Structure
Oxidation-Reduction
Oxides - chemistry
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
C-H ARYLATION
ALKYLATION
SITE-SELECTIVE SP
AROMATICS
PYRIDINES
ZINCATION
ASYMMETRIC ALLYLATION
BASE
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Summary:Azine N-oxides undergo highly regioselective metalation with TMPZnCl·LiCl under mild conditions. A palladium-catalyzed Negishi cross-coupling reaction of the resulting organozinc species with heteroaromatic bromides provides heterobiaryls specifically oxidized at one nitrogen position in up to 95% yield.
Bibliography:ObjectType-Article-1
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ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol203388j