Palladium‐Catalyzed Asymmetric C(sp3)−H Allylation of 2‐Alkylpyridines

The palladium‐catalyzed asymmetric side‐chain C(α)‐allylation of 2‐alkylpyridines, without using an external base, was developed. The high linear selectivities and enantioselectivities were achieved using new chiral diamidophosphite monodentate ligands. Given that the reaction conditions do not requ...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-07, Vol.57 (30), p.9465-9469
Main Authors: Murakami, Ryo, Sano, Kentaro, Iwai, Tomohiro, Taniguchi, Tohru, Monde, Kenji, Sawamura, Masaya
Format: Article
Language:English
Subjects:
Allyl compounds
allylation
asymmetric catalysis
Carbonyls
Chemical reactions
C−H activation
ligand design
Palladium
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Summary:The palladium‐catalyzed asymmetric side‐chain C(α)‐allylation of 2‐alkylpyridines, without using an external base, was developed. The high linear selectivities and enantioselectivities were achieved using new chiral diamidophosphite monodentate ligands. Given that the reaction conditions do not require an external base, this catalyst system enabled chemoselective C(α)‐allylation of 2‐alkylpyridines containing α‐carbonyl C−H bonds, which are more acidic than α‐pyridyl C−H bonds. No branching out: The palladium‐catalyzed asymmetric side‐chain C(α)‐allylation of 2‐alkylpyridines was developed. The high linear selectivities and enantioselectivities were achieved using a new chiral ligand. This catalyst system enabled chemoselective C(α)‐allylation of 2‐alkylpyridines containing α‐carbonyl C−H bonds, which are more acidic than α‐pyridyl C−H bonds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201802821