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A Simple Synthetic Route to Well‐Defined [Pd(NHC)Cl(1‐ t Bu‐indenyl)] Pre‐catalysts for Cross‐Coupling Reactions
Author(s) -
Liu Yaxu,
Scattolin Thomas,
Gobbo Alberto,
Beliš Marek,
Van Hecke Kristof,
Nolan Steven P.,
Cazin Catherine S. J.
Publication year - 2022
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202100840
Subject(s) - chemistry , catalysis , imes , acetone , medicinal chemistry , ligand (biochemistry) , base (topology) , combinatorial chemistry , coupling reaction , carbene , organic chemistry , mathematical analysis , biochemistry , receptor , mathematics
The development of robust, more efficient, general, easily accessible Pd(II)–NHC pre‐catalysts remains a key issue in cross‐coupling applications. A selection of well‐defined, air and moisture stable [Pd(NHC)Cl(1‐ t Bu‐indenyl)] (NHC=IPr, IPr Cl , IMes, SIMes, IPr*) pre‐catalysts have been synthesized in good to excellent yields by reacting [Pd(1‐ t Bu‐indenyl)(μ‐Cl)] 2 and various NHC⋅HCl precursors in the presence of the weak base K 2 CO 3 in green acetone. The synthesized Pd(II)‐NHC derivatives displayed excellent catalytic activity in classical Suzuki‐Miyaura and Buchwald–Hartwig reactions, especially when IPr Cl is employed as ancillary ligand. Additionally, in the challenging Suzuki‐Miyaura reaction between esters and arylboronic acids, the [Pd(IPr*)Cl(1‐ t Bu‐indenyl)] complex exhibited the optimum catalytic activity under very mild reaction conditions.