Ligand-assisted palladium-catalyzed C-H alkenylation of aliphatic amines for the synthesis of functionalized pyrrolidines

The development of a ligand-assisted Pd-catalyzed C-H alkenylation of aliphatic amines is reported. Our studies indicated that an amino-acid-derived ligand renders the C-H bond activation step reversible and promotes the traditionally difficult alkenylation process. The C(sp )-H alkenylation proceed...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2017-05, Vol.8 (5), p.3586-3592
Main Authors: He, Chuan, Gaunt, Matthew J
Format: Article
Language:English
Subjects:
Activation
Activation analysis
Aliphatic amines
Aliphatic compounds
Chemical bonds
Chemistry
Ligands
Palladium
Synthesis
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Summary:The development of a ligand-assisted Pd-catalyzed C-H alkenylation of aliphatic amines is reported. Our studies indicated that an amino-acid-derived ligand renders the C-H bond activation step reversible and promotes the traditionally difficult alkenylation process. The C(sp )-H alkenylation proceeds through a 5-membered-ring cyclopalladation pathway that allows access to complex aliphatic heterocycles that could be useful to practioners of synthetic and medicinal chemistry.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc00468k