Matches in SemOpenAlex for { <https://semopenalex.org/work/W2065561546> ?p ?o ?g. }
- W2065561546 endingPage "1605" @default.
- W2065561546 startingPage "1596" @default.
- W2065561546 abstract "Zerovalent carbene complexes of Pd containing the 1,3,4,5-tetramethylimidazol-2-ylidene ligand (tmiy) have been synthesized. Pd(COD)(alkene) (COD = cyclooctadiene) reacts with the nucleophilic carbene tmiy to produce the complexes Pd(tmiy)2(alkene) (alkene = maleic anhydride (MAH) (2), tetracyanoethylene (TCNE) (3)). Spectroscopic studies on the complexes provide strong evidence of the almost purely donor nature of the carbene ligand. Oxidative addition of hydrocarbyl halide and dihalide substrates to 2 and 3 yield the PdII derivatives Pd(tmiy)2(Ph)I (4), Pd(tmiy)2I2 (5), Pd(tmiy)2(4-nitrophenyl)I (6), and Pd(tmiy)2Br2 (7). The zerovalent Ni complex Ni(tmiy)2 was produced in situ from the reaction of Ni(COD)2 with tmiy, and the oxidative addition of organic halides yields Ni(tmiy)2(o-tolyl)Br (8), Ni(tmiy)2(Me)I (9), and Ni(tmiy)2I2 (10). X-ray crystal structures of complexes 8 and 10 are reported which reveal square-planar coordination with the carbene ligands inclined at significant angles to the coordination planes of the complexes. Metal to ligand bond distances are all indicative of the electron density induced on the metal center by the donor carbene ligands. Halide abstraction from 6 in the presence of n-butyl acrylate leads to migratory insertion of the olefin and elimination of the Heck coupling product. Under stoichiometric reaction conditions hydrocarbyl−imidazolium ions are also produced as byproducts. Selected complexes were tested as catalysts for the Heck reaction (Pd) and Suzuki coupling (Pd, Ni) and were found to be highly active. The observed reaction behavior is interpreted, and a mechanism for the Heck coupling is provided." @default.
- W2065561546 created "2016-06-24" @default.
- W2065561546 creator A5013000968 @default.
- W2065561546 creator A5021731130 @default.
- W2065561546 creator A5067323765 @default.
- W2065561546 creator A5082369913 @default.
- W2065561546 date "1999-04-01" @default.
- W2065561546 modified "2023-10-16" @default.
- W2065561546 title "Zerovalent Palladium and Nickel Complexes of Heterocyclic Carbenes: Oxidative Addition of Organic Halides, Carbon−Carbon Coupling Processes, and the Heck Reaction" @default.
- W2065561546 cites W1501926449 @default.
- W2065561546 cites W1537192859 @default.
- W2065561546 cites W1578648872 @default.
- W2065561546 cites W1964518283 @default.
- W2065561546 cites W1965792199 @default.
- W2065561546 cites W1967620487 @default.
- W2065561546 cites W1968142717 @default.
- W2065561546 cites W1969244248 @default.
- W2065561546 cites W1970799545 @default.
- W2065561546 cites W1975334991 @default.
- W2065561546 cites W1982604347 @default.
- W2065561546 cites W1987729460 @default.
- W2065561546 cites W2003951561 @default.
- W2065561546 cites W2008042892 @default.
- W2065561546 cites W2008273592 @default.
- W2065561546 cites W2009999932 @default.
- W2065561546 cites W2015354535 @default.
- W2065561546 cites W2015857976 @default.
- W2065561546 cites W2019579602 @default.
- W2065561546 cites W2025400518 @default.
- W2065561546 cites W2025745886 @default.
- W2065561546 cites W2031092862 @default.
- W2065561546 cites W2049337326 @default.
- W2065561546 cites W2056650687 @default.
- W2065561546 cites W2057235538 @default.
- W2065561546 cites W2064852383 @default.
- W2065561546 cites W2066607597 @default.
- W2065561546 cites W2069288102 @default.
- W2065561546 cites W2072168233 @default.
- W2065561546 cites W2085012740 @default.
- W2065561546 cites W2085921760 @default.
- W2065561546 cites W2107165605 @default.
- W2065561546 cites W2119688276 @default.
- W2065561546 cites W2129093859 @default.
- W2065561546 cites W2133414155 @default.
- W2065561546 cites W2141283145 @default.
- W2065561546 cites W2147607317 @default.
- W2065561546 cites W2167943526 @default.
- W2065561546 cites W2950500239 @default.
- W2065561546 doi "https://doi.org/10.1021/om9809771" @default.
- W2065561546 hasPublicationYear "1999" @default.
- W2065561546 type Work @default.
- W2065561546 sameAs 2065561546 @default.
- W2065561546 citedByCount "391" @default.
- W2065561546 countsByYear W20655615462012 @default.
- W2065561546 countsByYear W20655615462013 @default.
- W2065561546 countsByYear W20655615462014 @default.
- W2065561546 countsByYear W20655615462015 @default.
- W2065561546 countsByYear W20655615462016 @default.
- W2065561546 countsByYear W20655615462017 @default.
- W2065561546 countsByYear W20655615462018 @default.
- W2065561546 countsByYear W20655615462019 @default.
- W2065561546 countsByYear W20655615462020 @default.
- W2065561546 countsByYear W20655615462021 @default.
- W2065561546 countsByYear W20655615462022 @default.
- W2065561546 countsByYear W20655615462023 @default.
- W2065561546 crossrefType "journal-article" @default.
- W2065561546 hasAuthorship W2065561546A5013000968 @default.
- W2065561546 hasAuthorship W2065561546A5021731130 @default.
- W2065561546 hasAuthorship W2065561546A5067323765 @default.
- W2065561546 hasAuthorship W2065561546A5082369913 @default.
- W2065561546 hasConcept C116569031 @default.
- W2065561546 hasConcept C142653250 @default.
- W2065561546 hasConcept C155647269 @default.
- W2065561546 hasConcept C161790260 @default.
- W2065561546 hasConcept C168896768 @default.
- W2065561546 hasConcept C170493617 @default.
- W2065561546 hasConcept C178790620 @default.
- W2065561546 hasConcept C185592680 @default.
- W2065561546 hasConcept C188027245 @default.
- W2065561546 hasConcept C2776254738 @default.
- W2065561546 hasConcept C2777164566 @default.
- W2065561546 hasConcept C2779910884 @default.
- W2065561546 hasConcept C502130503 @default.
- W2065561546 hasConcept C55493867 @default.
- W2065561546 hasConcept C75473681 @default.
- W2065561546 hasConcept C94882840 @default.
- W2065561546 hasConceptScore W2065561546C116569031 @default.
- W2065561546 hasConceptScore W2065561546C142653250 @default.
- W2065561546 hasConceptScore W2065561546C155647269 @default.
- W2065561546 hasConceptScore W2065561546C161790260 @default.
- W2065561546 hasConceptScore W2065561546C168896768 @default.
- W2065561546 hasConceptScore W2065561546C170493617 @default.
- W2065561546 hasConceptScore W2065561546C178790620 @default.
- W2065561546 hasConceptScore W2065561546C185592680 @default.
- W2065561546 hasConceptScore W2065561546C188027245 @default.
- W2065561546 hasConceptScore W2065561546C2776254738 @default.
- W2065561546 hasConceptScore W2065561546C2777164566 @default.
- W2065561546 hasConceptScore W2065561546C2779910884 @default.