3287-02-3Relevant articles and documents
Syntheses, characterization, and structural studies of copper(I) complexes containing 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf) and their application in palladium-catalyzed Sonogashira coupling of aryl halides
Trivedi, Manoj,Singh, Gurmeet,Kumar, Abhinav,Rath, Nigam P.
, p. 13620 - 13629 (2014)
Four copper(i) complexes [Cu4(μ3-Cl) 4(μ-dtbpf)2] (1), [Cu6(μ3-Br) 4(μ2-Br)2(μ-dtbpf)3] (2), [Cu4(μ2-I)2(μ3-I) 2(μ-dtbpf)2] (3) and [Cu2(μ1- CN)2(κ2-dtbpf)2] (4) were prepared using CuX (X = Cl, Br, I, CN) and 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf) in 2:1 molar ratio in DCM-MeOH (50:50 V/V) at room temperature. These complexes were characterized by elemental analyses, IR, 1H and 31P NMR, ESI+-MS and electronic absorption spectroscopy. Molecular structures of the complexes 1, 2 and 3 were determined crystallographically. Complexes 1 and 3 are tetrameric Cu(i) pseudo-cubane like structures with a Cu4Cl4 core, and a stepped cubane-like structure with a Cu4I4 core, respectively, whereas complex 2 shows a trimeric copper(i) framework containing two [Cu3(μ 3-Br)2(μ2-Br)] units that are bridged by three bidentate μ-dtbpf ligands. Each [Cu3(μ3-Br) 2(μ2-Br)] unit forms a pyramid with one copper atom at the apex and one of the triangular faces capped by one bromine atom. All the complexes were found to be efficient catalysts for the Sonogashira reaction. The coupling products were obtained in moderate to good yields (58-99%) using Pd loadings of 0.2 mol% as well as complex loading of 0.1 mol%. The 31P NMR studies show that all the complexes are unstable during the course of tandem catalytic reaction and the dtbpf ligand migrates from copper(I) to palladium(II), which promotes palladium Sonogashira cross-coupling of activated and non-activated aryl halides. the Partner Organisations 2014.
A Ni(OAc)2·4H2O-catalysed Sonogashira-type coupling reaction of aryl iodides and terminal alkynes in the presence of CuI
Yang, Hailong,Zhu, Yan,Sun, Peng,Yan, Hong,Lu, Linhua,Wang, Shouguo,Mao, Jincheng
, p. 437 - 440 (2012)
An effective and promising Ni/Cu catalytic system for the coupling of aryl iodides with various terminal alkynes has been developed. For the first time the readily available chiral amino alcohol has been employed as the ligand for the Pd-free Sonogashira
SYNTHESIS AND REDUCTIVE ELIMINATION OF TRIARYLBIS(PHENYLETHYNYL)ANTIMONY (V)
Akiba, Kin-ya,Okinaka, Takaaki,Nakatani, Masayuki,Yamamoto, Yohsuke
, p. 3367 - 3368 (1987)
Triarylbis(phenylethynyl)antimony (V) (1a-1c) were synthesized from triarylantimony dibromide and lithium phenylacetylide.Thermolytic reductive elimination of 1a-1c took place at 110 deg C and the aryl-alkynyl coupling product (3) increased as the aryl group became more electronegative.The result is consistent with the apical-apical coupling from the trigonal bipyramidal structures, which was predicted to be symmetry-allowed by Hoffmann.
The nickel-catalyzed Sonogashira-Hagihara reaction
Beletskaya, Irina P.,Latyshev, Gennadij V.,Tsvetkov, Alexey V.,Lukashev, Nikolai V.
, p. 5011 - 5013 (2003)
The Sonogashira-Hagihara coupling of terminal acetylenes with aryl iodides in the presence of a nickel catalyst and CuI was investigated. The reaction proceeds rapidly in aqueous dioxane in the presence of Ni(PPh3)2Cl2 wit
Pd nanoparticles catalyst supported on TMU-16-NH2 metal-organic framework for Sonogashira cross-coupling reaction
Alinezhad, Heshmatollah,Ghasemi, Shahram,Kiani, Ameneh
, (2021/12/10)
The current article presented the synthesis and characterization of a novel, unique, and effective heterogeneous catalytic system, based on a metal-organic framework named Pd@TMU-16-NH2 with high catalytic performance. Also, the application of
Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water
Min, Qingwang,Miao, Penghua,Chu, Deyu,Liu, Jinghan,Qi, Meijuan,Kazemnejadi, Milad
, p. 3030 - 3047 (2021/02/16)
A new versatile and recyclable NHC ligand precursor has been developed with ligand, base, and solvent functionalities for the efficient Pd-catalyzed Heck, Suzuki and Sonogashira cross-coupling reactions under mild conditions. Furthermore, NHC ligand precursor was immobilized on magnetite and its catalytic activity was also evaluated towards the coupling reactions as a heterogeneous catalyst. The NHC ligand precursor was prepared with imidazolium functionalization of TCT followed by a simple ion exchange by hydroxide ions. However, the results revealed an excellent catalytic activity for the both homogeneous and heterogeneous catalytic systems. 1.52?g.cm?3 and 1194 cP was obtained for the density and viscosity of the NHC ligand precursor respectively. On the other hand, the heterogeneous type could be readily recovered from the reaction mixture and reused for several times while preserving its properties. Heterogeneous nature of the magnetic catalyst was studied by hot filtration, mercury poisoning, and three-phase tests. High to excellent yields were obtained for all entries for the both homogeneous and heterogeneous catalysts, which reflects the high consistency of the catalyst. Graphic Abstract: [Figure not available: see fulltext.]
Si-Gly-CD-PdNPs as a hybrid heterogeneous catalyst for environmentally friendly continuous flow Sonogashira cross-coupling
Cravotto, Giancarlo,Ferlin, Francesco,Martina, Katia,Menzio, Janet,Sciosci, Daniele,Vaccaro, Luigi,Valentini, Federica
supporting information, p. 7210 - 7218 (2021/09/28)
We have reported a waste-minimized protocol for the Sonogashira cross-coupling exploiting the safe use of a CPME/water azeotropic mixture and the utilization of a heterogeneous hybrid palladium catalyst supported onto a silica/β-cyclodextrin matrix in con
