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
Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes
Lokolkar, Manjunath S.,Mane, Pravin A.,Dey, Sandip,Bhanage, Bhalchandra M.
, (2021/06/25)
This work reports Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction of phenyl propiolic acid and 2-butynoic acid with various iodoarenes. These palladium aryl dithiolate complexes were synthesized and characterized by 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, melting point, and elemental analysis (CHNS). Synthetic utility for the reported protocol is explored for the effect of various functional groups on the yield of corresponding heteroaryl alkynes. The current protocol showed excellent catalytic activity towards decarboxylative alkynylation reaction with high turn-over number (TON) up to 105 and turn-over frequency (TOF) up to 104 h?1. The catalyst could be recycled up to six recycles without losing its catalytic activity. The in situ generation of palladium nanoparticles (PdNPs) was observed after the third recycle, and the amount was significant after the sixth recycle, which were confirmed and characterized by powder X-ray diffraction (XRD), scanning electron microscope (SEM), and energy-dispersive X-ray (EDX) analysis and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of the reaction is attributed to the formation of PdNPs.
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
