Changing the Palladium Coordination to Phosphinoimidazolines with a Remote Triazole Substituent

Phosphinoimidazoline (PHIM) ligands bearing a triazolylmethyl substituent at the sp3 nitrogen atom in the imidazoline ring lead to highly improved enantioselectivity (up to 99% ee) in allylic substitution reactions with respect to analogous ligands with substituents lacking the triazole unit. NMR an...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2011-12, Vol.353 (18), p.3255-3261
Main Authors: de la Fuente, Verónica, Marcos, Rocío, Cambeiro, Xacobe C., Castillón, Sergio, Claver, Carmen, Pericàs, Miquel A.
Format: Article
Language:English
Subjects:
allylic substitution
asymmetric catalysis
Bearing
Catalysis
Chemistry
Coordination compounds
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Imidazoline
Inorganic chemistry and origins of life
Ligands
Nitrogen atoms
Organic chemistry
Palladium
phosphinoimidazoline ligands
Preparations and properties
Synthesis (chemistry)
triazole ligands
Triazoles
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Summary:Phosphinoimidazoline (PHIM) ligands bearing a triazolylmethyl substituent at the sp3 nitrogen atom in the imidazoline ring lead to highly improved enantioselectivity (up to 99% ee) in allylic substitution reactions with respect to analogous ligands with substituents lacking the triazole unit. NMR and theoretical studies support a shift in the coordination mode of the PHIM ligand to palladium, triggered by a very favourable interaction with the triazole unit.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201100684