Regio‐ and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H‐Pyrans: Heck Coupling of Monocyclopropanated Heterocycles

A palladium‐catalyzed coupling between aryl halides and monocyclopropanated pyrroles or furans has been developed, leading to valuable six‐membered N‐ and O‐heterocycles. As the key step, a selective cleavage of the non‐activated endocyclic C−C bond of the 2‐heterobicyclo‐[3.1.0]hexane framework is...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-03, Vol.58 (11), p.3594-3598
Main Authors: Yedoyan, Julietta, Wurzer, Nikolai, Klimczak, Urszula, Ertl, Thomas, Reiser, Oliver
Format: Article
Language:English
Subjects:
2H-pyrans
Aromatic compounds
arylpyridines
Coupling
dihydropyridines
donor–acceptor cyclopropanes
Furans
Halides
Heck coupling
Palladium
Pesticides
Pyridines
Pyrroles
Stereoselectivity
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Summary:A palladium‐catalyzed coupling between aryl halides and monocyclopropanated pyrroles or furans has been developed, leading to valuable six‐membered N‐ and O‐heterocycles. As the key step, a selective cleavage of the non‐activated endocyclic C−C bond of the 2‐heterobicyclo‐[3.1.0]hexane framework is achieved. The developed method offers access to highly functionalized piperidines, pyridines, and pyrans that are challenging to access by traditional methods. Heck‐type arylation of cyclopropanated furans and pyrroles proceeds with ring expansion via the unactivated cyclopropyl bond, giving rise to arylated diyhdropyridines, pyridines, and 2H‐pyrans.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201813716