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(3))-H alkenylation proce...

Full description

Saved in:
Bibliographic Details
Published inChemical science (Cambridge) Vol. 8; no. 5; pp. 3586 - 3592
Main Authors He, Chuan, Gaunt, Matthew J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.05.2017
Subjects
Activation
Activation analysis
Aliphatic amines
Aliphatic compounds
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Ligands
Palladium
Physical Sciences
Science & Technology
Synthesis
UNACTIVATED C(SP)-H BONDS
ROOM-TEMPERATURE
CROSS-COUPLING REACTIONS
TRANSITION-METAL-COMPLEXES
ENANTIOSELECTIVE SYNTHESIS
ARYLBORON REAGENTS
NATURAL-PRODUCTS
CARBON-HYDROGEN BONDS
SELECTIVE ALKENYLATION
ACTIVATION REACTIONS
Online AccessGet full text

Cover

More Information
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(3))-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.
Bibliography:researchfish
UKRI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc00468k