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N‐Heterocyclic Carbene–Palladium Complexes [(NHC)Pd(acac)Cl]: Improved Synthesis and Catalytic Activity in Large‐Scale Cross‐Coupling Reactions
Author(s) -
Marion Nicolas,
de Frémont Pierre,
Puijk Iris M.,
Ecarnot Elise C.,
Amoroso Dino,
Bell Andrew,
Nolan Steven P.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700195
Subject(s) - imes , chemistry , catalysis , carbene , palladium , medicinal chemistry , coupling reaction , ketone , organic chemistry
From two commercially available starting materials, improved one‐step, multigram‐scale syntheses of [(IPr)Pd(acac)Cl] [IPr= N , N′ ‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene; acac=acetylacetonate] and [(IMes)Pd(acac)Cl] [IMes= N , N′ ‐bis(2,4,6‐trimethylphenyl)imidazol‐2‐ylidene] are described. The catalytic activity of both complexes in cross‐coupling reactions has been examined. The most active pre‐catalyst, [(IPr)Pd(acac)Cl], has allowed for efficient large‐scale (10 mmol) Buchwald–Hartwig and α‐ketone arylation reactions to be carried out.