A Solution to the 2-Pyridyl Organometallic Cross-Coupling Problem:  Regioselective Catalytic Direct Arylation of Pyridine N-Oxides

Direct arylation reactions of pyridine N-oxides occur in excellent yield with complete selectivity for the 2-position with a wide range of aryl bromides. This reactivity permits the use of inexpensive, commercially available, and bench-stable pyridine N-oxides as replacements for problematic 2-metal...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 127; no. 51; pp. 18020 - 18021
Main Authors Campeau, Louis-Charles, Rousseaux, Sophie, Fagnou, Keith
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.12.2005
Amer Chemical Soc
Subjects
Chemical reactivity
Chemistry
Chemistry, Multidisciplinary
Exact sciences and technology
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
PALLADIUM
ACTIVATION
COMPLEXES
ARYL
EFFICIENT DEOXYGENATION
H BOND FUNCTIONALIZATION
ZINC
Platinoid Compounds
Arylation
Catalytic reaction
Regioselectivity
Nitrogen heterocycle
Catalyst selectivity
Transition metal Compounds
Six membered ring
Nitrone
Experimental study
Catalyst activity
Catalyst
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Summary:Direct arylation reactions of pyridine N-oxides occur in excellent yield with complete selectivity for the 2-position with a wide range of aryl bromides. This reactivity permits the use of inexpensive, commercially available, and bench-stable pyridine N-oxides as replacements for problematic 2-metallapyridines in palladium-catalyzed cross-coupling reactions.
Bibliography:istex:DBD5679903F0D8481E4C12F9A9EE2C4C248A5CEA
ark:/67375/TPS-0L02R0Z6-H
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SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja056800x