115021-39-1Relevant articles and documents
A palladium/perfluoroalkylated pyridine catalyst for sonogashira reaction of aryl bromides and chlorides in a fluorous biphasic system
Yi, Wen-Bin,Cai, Chun,Wang, Xin
, p. 3445 - 3448 (2007)
Palladium perfluorooctanesulfonate [Pd(OPf)2] catalyses the highly efficient Sonogashira reaction of aryl bromides and chlorides in the presence of a catalytic amount of perfluoroalkylated pyridine as a ligand in a fluorous biphasic system (FBS) composed of toluene and perfluorodecalin. The reaction can be performed under phosphane-, copper- and DMF-free conditions in an air atmosphere. By simple separation of the fluorous phase containing palladium/perfluoroalkylated pyridine catalyst, the reaction can be repeated several times. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
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)
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.
Copper-free Sonogashira reactions catalyzed by a palladium(II) complex bearing pyrenealdehyde thiosemicarbazonate under ambient conditions
Prabhu, Rupesh Narayana,Pal, Samudranil
, p. 5252 - 5256 (2015)
Convenient synthesis of a new square-planar mononuclear palladium(II) complex bearing N,S-donor 1-pyrenaldehyde 4-methyl-3-thiosemicarbazonate (L-) as ligand is described. The identity of the complex has been established as [Pd(L)Cl(PPh3/
Anthracen-9-ylmethylene-(4-methoxyphenyl)amine: efficient promoter for silver-free palladium-catalyzed aerobic oxidative Sonogashira reactions
Lakshmipraba, Jagadeesan,Prabhu, Rupesh Narayana,Dhayabaran, Victor Violet
, p. 325 - 331 (2020)
An efficient protocol for the synthesis of unsymmetrical substituted diarylacetylenes by the C(sp2)–C(sp) cross-coupling reactions of substituted phenylacetylenes and electronically different arylboronic acids has been developed. Anthracen-9-ylmethylene-(4-methoxyphenyl)amine was employed as an efficient promoter in this Pd(OAc)2-catalyzed oxidative Sonogashira reaction in air in the absence of silver salt under optimized reaction conditions. The impact of reaction parameters such as solvent, base, reaction temperature and time in this silver-free aerobic oxidative Sonogashira cross-coupling reaction was also evaluated. Electron-deficient phenylacetylenes, which are sluggish coupling partners in the traditional Sonogashira reaction, underwent coupling in this protocol. The catalytic system is inexpensive, effortlessly attainable and highly flexible for functionalized phenylacetylenes and arylboronic acids. Graphic abstract: [Figure not available: see fulltext.].
Magnetically retrievable N-heterocyclic carbene-silver complex with wingtip ferrocenyl group for Sonogashira coupling
Naikwade, Altafhusen,Bansode, Prakash,Rashinkar, Gajanan
, p. 112 - 122 (2018)
A new magnetically retrievable N-heterocyclic carbene-silver complex with wingtip ferrocenyl group has been prepared by multi-step procedure. The formation of complex was confirmed on the basis of analytical techniques such as FT-IR, Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), X-Ray diffraction (XRD), transmission electron microscopy (TEM) and VSM (vibrating sample magnetometer) analysis. The complex was successfully employed as an efficient heterogeneous catalyst for Sonogashira coupling reaction of aryl halides with terminal alkynes. The complex could be separated easily by applying external magnet. The reusability studies revealed that complex can be reused up to eight times without significant decrease in catalytic activity.
Bimetallic Ni/Cu mesoporous silica nanoparticles as an efficient and reusable catalyst for the Sonogashira cross-coupling reactions
Nasresfahani, Zahra,Kassaee, Mohamad Z.
, (2021)
A bimetallic mesoporous system (Ni/Cu-MCM-41) has been developed and evaluated as an efficient catalyst for the Sonogashira cross-coupling reaction, under palladium-free conditions. In this new methodology, a wide range of aryl halides react with phenylacetylene to give the corresponding disubstituted alkynes in good yields. Moreover, the present catalytic system is desired because of its high efficiency, easy preparation, low cost, high activity, and good recyclability.
A nickel(II) thiosemicarbazonato complex: synthesis, structure, electrochemistry, and application in catalytic coupling of terminal alkynes with arylboronic acids
Prabhu, Rupesh Narayana,Lakshmipraba, Jagadeesan
, p. 579 - 585 (2017)
Abstract: A simple route for the synthesis of a new square-planar nickel(II) complex of 2-((3-methylthiophen-2-yl)methylene)hydrazinecarbothioamide is described. Elemental analysis, solution conductivity, and spectral measurements were used to authenticate the composition of the complex. In addition, the X-ray crystal structure of the complex was obtained. Each of the two ligands of the centrosymmetric structure is coordinated to the metal center via the azomethine N and the thioimidate S atoms, forming five-membered chelate rings. Infrared and NMR spectroscopic features of the complex are consistent with its molecular structure. The complex displays a quasi-reversible reduction with E1/2 of ?0.83?V (ΔEp 160?mV), indicating that the ligand system can stabilize the Ni(I) oxidation state. The complex acts as an active catalyst for the C–C coupling of aryl acetylenes with arylboronic acids containing a variety of substituents. The influence of solvent, base, reaction temperature, and catalyst loading on the C–C coupling reaction was evaluated. Graphical abstract: A new square-planar nickel(II) complex bearing 2-((3-methylthiophen-2-yl)methylene)-hydrazinecarbothioamide was synthesized and characterized by elemental analysis, FTIR, NMR, and single-crystal X-ray crystallographic technique. Cyclic voltammetric study indicates stabilization of Ni(I) oxidation state. The complex acts as an effective catalyst for the carbon–carbon cross-coupling reaction of substituted phenylacetylenes with various arylboronic acids under optimized conditions.[Figure not available: see fulltext.].
