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Regio‐ and Stereoselective Synthesis of Functionalized Dihydropyridines, Pyridines, and 2H‐Pyrans: Heck Coupling of Monocyclopropanated Heterocycles
Author(s) -
Yedoyan Julietta,
Wurzer Nikolai,
Klimczak Urszula,
Ertl Thomas,
Reiser Oliver
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813716
Subject(s) - stereoselectivity , chemistry , aryl , heck reaction , halide , palladium , combinatorial chemistry , bond cleavage , organic chemistry , catalysis , alkyl
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.