1942-31-0Relevant articles and documents
Seyferth,Wehman
, p. 5520,5521 (1970)
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
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.
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.
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
Novel scorpionate-type triscarbene ligands and their silver and gold complexes
Biffis, Andrea,Lobbia, Giancarlo Gioia,Papini, Grazia,Pellei, Maura,Santini, Carlo,Scattolin, Elena,Tubaro, Cristina
, p. 3760 - 3766 (2008)
New silver(I) carbene complexes were obtained starting from the N-heterocyclic carbene ligand precursors {[HB(RImH)3]Br2} (R = Bn, Mes and t-Bu) and {[HC(MeBImH)3](BF4)3}, by treatment of the imidazolium salt with Ag2O. Use of the tris-imidazolylborate precursors resulted in stable, well-characterized trimetallic complexes of general formula {Ag3[HB(RIm)3]2}Br, which were successfully employed as carbene transfer reagents in the synthesis of related gold(I) complexes by transmetallation. The silver complexes also proved to be active catalysts of the coupling of aryl iodides with terminal alkynes (the Sonogashira reaction), although related bimetallic silver complexes were found to exhibit enhanced reactivity.
Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions
Liu, Qingxiang,Zhang, Xiantao,Zhao, Zhixiang,Li, Xinying,Zhang, Wei
supporting information, p. 605 - 613 (2021/02/01)
Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.
Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent
Karimi, Sabah,Masteri-Farahani, Majid,Niakan, Mahsa,Shekaari, Hemayat
, (2020/10/02)
Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.
Glycosyl Triazole Ligand for Temperature-Dependent Competitive Reactions of Cu-Catalyzed Sonogashira Coupling and Glaser Coupling
Mishra, Nidhi,Singh, Sumit K.,Singh, Anoop S.,Agrahari, Anand K.,Tiwari, Vinod K.
, p. 17884 - 17895 (2021/12/17)
Glycosyl triazoles have been introduced as efficient ligands for the Cu-catalyzed Sonogashira reaction to overcome the challenges of sideways homocoupling reactions in Cu catalysis in this reaction. The atmospheric oxygen in a sealed tube did not affect t
