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Insights into the Catalytic Activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPr Cl , IPr Br ) Complexes in the Suzuki–Miyaura Reaction
Author(s) -
Izquierdo Frédéric,
Zinser Caroline,
Minenkov Yury,
Cordes David B.,
Slawin Alexandra M. Z.,
Cavallo Luigi,
Nahra Fady,
Cazin Catherine S. J.,
Nolan Steven P.
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201701279
Subject(s) - carbene , chemistry , catalysis , steric effects , palladium , medicinal chemistry , halogenation , suzuki reaction , coupling reaction , stereochemistry , organic chemistry
The influence of C 4,5 ‐halogenation on palladium N‐heterocyclic carbene complexes and their activity in the Suzuki–Miyaura reaction were investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPr Cl and IPr Br ligands (IPr=1,3‐bis(2,6‐diisopropyl‐phenyl)imidazol‐2‐ylidene; cin=cinnamyl) were synthesized. After determining the electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr) (cin)Cl]. The three palladium complexes were studied by using DFT calculations to delineate their behavior in the activation step leading to the putative 12‐electron active catalyst. Experimentally, their catalytic activity in the Suzuki–Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.