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Mizoroki–Heck Cross‐Coupling of Acrylate Derivatives with Aryl Halides Catalyzed by Palladate Pre‐Catalysts
Author(s) -
Islam Mohammad Shahidul,
Nahra Fady,
Tzouras Nikolaos V.,
Barakat Assem,
Cazin Catherine S. J,
Nolan Steven P.,
AlMajid Abdullah Mohammed
Publication year - 2019
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.201901075
Subject(s) - chemistry , aryl , catalysis , halide , carbene , heck reaction , acrylate , coupling reaction , solvent , combinatorial chemistry , aryl halide , organic chemistry , palladium , polymer chemistry , polymer , copolymer , alkyl
The Mizoroki–Heck (MH) reaction involving aryl halides with various acrylates and acrylamides has been studied using air and moisture‐stable imidazolium‐based palladate pre‐catalysts. These pre‐catalysts can be converted into Pd‐NHC species (NHC = N‐heterocyclic carbene) under catalytic conditions and are capable of facilitating the Mizoroki–Heck reaction of aryl halides with various acrylates. The effects of solvent, catalyst loading, temperature and bases on the reaction outcome have been investigated. Various coupling partners were tolerated under the optimal reaction conditions catalyzed by palladate 1 , [SIPr · H][Pd(η 3 ‐2‐Me‐allyl)Cl 2 ]. The efficiency of the optimized synthetic methodology was tested on various aryl halides and substituted acrylates as well as acrylamides. The MH reaction yielded the coupled products in good to excellent isolated yields (up to 98%).