1942-31-0Relevant articles and documents
Group 10 metal complexes with chelating macrocyclic dicarbene ligands bearing a 2,6-lutidinyl bridge: Synthesis, reactivity, and catalytic activity
Biffis, Andrea,Cipani, Matteo,Bressan, Edoardo,Tubaro, Cristina,Graiff, Claudia,Venzo, Alfonso
, p. 2182 - 2188 (2014)
Palladium(II) and platinum(II) complexes of the title ligands have been prepared; the two carbene moieties of the ligand coordinate to the metal in cis fashion, while the bridging pyridyl group remains outside the metal coordination sphere but close to the metal center. In this peculiar situation, the pyridyl group can assist the oxidation of the metal center to the +IV oxidation state upon coordination to the metal in the product. Furthermore, the pyridyl group is found to promote the catalytic role of the palladium(II) complexes in copper- and amine-free Sonogashira reactions.
Generalized fabrication of multifunctional nanoparticle assemblies on silica spheres
Kim, Jaeyun,Lee, Ji Eun,Lee, Jinwoo,Jang, Youngjin,Kim, Sang-Wook,An, Kwangjin,Yu, Jung Ho,Hyeon, Taeghwan
, p. 4789 - 4793 (2006)
Sequential decoration of silica spheres by covalent bonding of magnetite nanoparticles (blue) and attachment of functional nanoparticles of Au, CdSe/ZnS, or Pd (red) afforded multifunctional assemblies exhibiting combinations of magnetism with surface pla
Nonpolar biphasic catalysis: Sonogashira and Suzuki coupling of aryl bromides and chlorides
Datta, Anupama,Plenio, Herbert
, p. 1504 - 1505 (2003)
Palladium-phosphine catalysts which are phase-tagged with soluble poly(4-methylstyrene) can be used for efficient carbon-carbon coupling reactions by nonpolar biphasic catalysis with high recyclability as evidenced by high yields, constant tof of the cata
Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki-Miyaura and Sonogashira coupling reactions
Boubakri,Yasar,Dorcet,Roisnel,Bruneau,Hamdi,Ozdemir
, p. 5105 - 5113 (2017)
A new palladium complex series with N-heterocyclic carbene (NHC), pyridine and phosphine ligands, PdCl2(L)NHC (2a-c)(L = NHC), PdCl2(L1)NHC(3a-c)(L1 = pyridine), PdCl2(L2)NHC(4a-c)(L2 = triphenylphosphine) was synthesised and fully characterized. The catalytic activities of these complexes were screened for the Sonogashira and Suzuki-Miyaura reactions between arylhalides and phenylacetylene, and phenylboronic acid, respectively. The results pointed out that the carbene/phosphine complexes 4a-c exhibited excellent catalytic activities as compared to 2a-c, 3a-c, and the well-known systems for the palladium-catalysed Sonogashira reaction. The reactivity of 4a-c in these preliminary Sonogashira coupling tests seems to be higher than that of previously reported catalytic systems based on Pd(NHC) moieties. These new palladium NHC complexes are among the first reported palladium catalysts that are efficient for catalysing the Sonogashira reaction from arylchloride substrates.
Palladium(II) phosphine-ylide complexes as highly efficient pre-catalysts in additive- and amine-free Sonogashira coupling reactions performed under aerobic and low Pd loading conditions
Sabounchei, Seyyed Javad,Ahmadi, Mohsen,Nasri, Zahra,Shams, Esmaeil,Panahimehr, Mohammad
, p. 4656 - 4660 (2013)
Moisture and air-stable, robust palladacycle phosphine-ylide complexes as catalyst precursors were used in additive- and amine-free Sonogashira cross-coupling reactions. Various aryl halides were coupled with phenylacetylene in DMF, under air, in the pres
A simple building-block route to (phosphanyl-carbene)palladiuni complexes via intermolecular addition of functionalised phosphanes to isocyanides
Eberhard, Michael R.,Van Vliet, Bart,Pachon, Laura Duran,Rothenberg, Gadi,Easthani, Graham,Kooijnian, Huub,Spek, Anthony L.,Elsevier, Cornells J.
, p. 1313 - 1316 (2009)
We present a straightforward protocol for making (phosphanyl-carbene) PdII complexes. These complexes have bidentate ligands containing an acyclic diamino- or aminooxy-carbene and a phosphane. The synthesis gives good yields (typically 70-90%) for a variety of complexes (22 compounds). Moreover, it does not require the synthesis of imid azolium salts nor the a priori generation of free carbenes. Three of the new complexes were tested as catalysts for Son-ogashira and Hay coupling reactions, with good yields and selectivities. Wiley-VCH Verlag GmbH & Co, KGaA.
Sonogashira cross-coupling using carbon aerogel doped with palladium nanoparticles; a recoverable and reusable catalyst
Soler, Roger,Cacchi, Sandro,Fabrizi, Giancarlo,Forte, Giovanni,Martin, Laura,Martinez, Sandra,Molins, Elies,Moreno-Manas, Marcial,Petrucci, Francesco,Roig, Anna,Sebastian, Rosa M.,Vallribera, Adelina
, p. 3068 - 3072 (2007)
The Sonogashira cross coupling of aryl iodides with terminal alkynes has been carried out in the presence of carbon aerogels doped with metallic palladium nanoparticles. Coupling products have been isolated in excellent yields and the catalyst system can
Comparison between polyethylenglycol and imidazolium ionic liquids as solvents for developing a homogeneous and reusable palladium catalytic system for the Suzuki and Sonogashira coupling
Corma, Avelino,García, Hermenegildo,Leyva, Antonio
, p. 9848 - 9854 (2005)
The carbapalladacycle complex of 4-hydroxyacetophenone oxime is a highly active palladium catalyst to effect the Suzuki coupling of aryl chlorides and other C-C forming reactions in water. In an attempt to develop a reusable, homogeneous system based on this complex, its stability against prolonged heating in different ionic liquids and polyethylenglycol (PEG) has been studied. It was found that the palladium complex decomposes in water, 1-butyl-1-methylimidazolium hexafluorophosphate and 1-butyl-1-methylimidazolium chloride to form palladium nanoparticles in the first two cases and PdCl 42- in the third case. In contrast, this cyclic palladium complex was stable upon extended heating in 1-butyl-2,3-dimethylimidazolium hexafluorophosphate and in PEG. The activity of this complex for the Suzuki and Sonogashira correlates with the stability of the complex, the activity in PEG being higher than any of the ionic liquids tested. Although the carbapalladacycle complex also decomposes in PEG upon reaction, the resulting Pd nanoparticles (2-5 nm size) are stabilized by PEG acting as ligand. In this way, a reusable, homogeneous system in PEG has been developed that is able to effect the Suzuki and Sonogashira couplings without the need of copper and phosphorous ligands, working at the open air.
Designed Synthesis of Atom-Economical Pd/Ni Bimetallic Nanoparticle-Based Catalysts for Sonogashira Coupling Reactions
Son, Seung Uk,Jang, Youngjin,Park, Jongnam,Na, Hyon Bin,Park, Hyun Min,Yun, Hyung Joong,Lee, Jouhahn,Hyeon, Taeghwan
, p. 5026 - 5027 (2004)
We synthesized Ni/Pd core/shell nanoparticles from the consecutive thermal decomposition of metal-surfactant complexes. The nanoparticle catalyst was atom-economically applied for various Sonogashira coupling reactions. Copyright
Designed synthesis of Au/Ag/Pd trimetallic nanoparticle-based catalysts for sonogashira coupling reactions
Venkatesan,Santhanalakshmi
, p. 12225 - 12229 (2010)
Pdnp and Pd containing trimetallic nanoparticles (tnp) are synthesized by chemical methodwith cetyltrimethylammonium bromide as the capping agent. Compositionally, four different tnp are prepared and the particle sizes are characterized by UV-vis spectra,
