[Pd(IPr)(3-Cl-pyridinyl)Cl2]: A Novel and Efficient PEPPSI Precatalyst

The preparation of the novel, well-defined [Pd(IPr*)(3-Cl-pyridinyl)Cl2] complex is described. The steric parameters of the ligand as well as its reactivity in the Buchwald–Hartwig amination were directly compared to other [Pd(NHC)(3-Cl-pyridinyl)Cl2] and [Pd(IPr*)(LX)Cl)] precatalysts (LX = cinnamy...

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Published inOrganometallics Vol. 31; no. 19; pp. 6947 - 6951
Main Authors Chartoire, Anthony, Frogneux, Xavier, Boreux, Arnaud, Slawin, Alexandra M. Z, Nolan, Steven P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.10.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
ORTHO-SUBSTITUTED BIARYLS
N-HETEROCYCLIC CARBENE
CYCLOPALLADATED FERROCENYLIMINE
HINDERED ARYL CHLORIDES
COUPLING REACTION
CATALYZED ALPHA-ARYLATION
PRE-CATALYST
NHC-PD(II)-IM NHC
IM=1-METHYLIMIDAZOLE COMPLEXES
SUZUKI-MIYAURA
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Summary:The preparation of the novel, well-defined [Pd(IPr*)(3-Cl-pyridinyl)Cl2] complex is described. The steric parameters of the ligand as well as its reactivity in the Buchwald–Hartwig amination were directly compared to other [Pd(NHC)(3-Cl-pyridinyl)Cl2] and [Pd(IPr*)(LX)Cl)] precatalysts (LX = cinnamyl or acac). The title complex exhibits similar catalytic activity to [Pd(NHC)(3-Cl-pyridinyl)Cl2] congeners (NHC = IPr and SIPr) at room temperature. However, it also showed improved reactivity at low catalyst loading and high temperature (as low as 0.025 mol %). On the other hand, it proved to be as efficient as the previously reported [Pd(IPr*)(cinnamyl)Cl] complex, pointing to the most likely existence of a similar catalytically active species.
ISSN:0276-7333
1520-6041
DOI:10.1021/om300725f