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
Versatile and an efficient Sonogashira coupling reaction catalyzed with modified Pd-functionalized TMU-16 as a novel and reusable nanocatalyst
Alinezhad, Heshmatollah,Ghasemi, Shahram,Kiani, Ameneh
, (2021/07/24)
This research paper, reports the preparation of palladium impregnated [Zn2(BDC)2(4-bpdh)]3DMF (Pd@TMU-16) with a simple liquid impregnation-reduction method as a novel and efficient catalyst with the high catalytic performance for co
A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope
Valentini, Federica,Ferlin, Francesco,Tomarelli, Elena,Mahmoudi, Hamed,Bagherzadeh, Mojtaba,Calamante, Massimo,Vaccaro, Luigi
, p. 3359 - 3366 (2021/07/28)
Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.
