Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 24, Pages 5950-5955Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900313
Keywords
aryl tosylates; C-C coupling; Mizoroki-Heck coupling; heterocycles; palladium
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Funding
- Danish National Research Foundation
- Lundbeck Foundation
- Carlsberg Foundation
- AstraZeneca group
- Aarhus University
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Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.
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