13667-12-4Relevant articles and documents
Palladium-catalyzed decarboxylative coupling reaction with alkynyl carboxylic acids and arylsiloxanes
Jang, Jisun,Raja, Gabriel Charles Edwin,Lee, Ju-Hyeon,Son, Yujeong,Kim, Jimin,Lee, Sunwoo
, p. 4581 - 4584 (2016)
A decarboxylative coupling reaction for alkynyl carboxylic acids and arylsiloxanes was developed using a palladium catalyst. This method provided the desired coupled products in moderate to good yields by reacting the alkynyl carboxylic acids and arylsiloxanes with Pd(dba)2(1.0?mol?%), 1,1-bis(diphenylphosphino)methane (1.0?mol?%), and AgF2(2.0?equiv) at 60?°C for 6?h.
Aggregates of a hetero-oligophenylene derivative as reactors for the generation of palladium nanoparticles: a potential catalyst in the Sonogashira coupling reaction under aerial conditions
Walia, Preet Kamal,Pramanik, Subhamay,Bhalla, Vandana,Kumar, Manoj
, p. 17253 - 17256 (2015)
The utilization of Pd nanoparticles stabilized by aggregates of hetero-oligophenylene derivative 3 as an excellent catalyst in a copper/amine free Sonogashira coupling reaction under aerial conditions at room temperature has been demonstrated.
Copper(I) complexes of 2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile and triphenylphosphine ligands: synthesis, characterization, luminescence and catalytic properties
Devkule,Chavan
, p. 347 - 356 (2017)
Some mixed ligand copper(I) complexes of general formula [Cu(L)(PPh3)3]X (X?=?Cl (1), ClO4 (2), BF4 (3) or PF6 (4); L?=?2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile) were prepared and characterized by physicochemical and spectroscopic methods. A single-crystal X-ray diffraction study of [Cu(L)(PPh3)3]CIO4 (2) revealed that the copper atom is four coordinated in a distorted tetrahedral geometry. Electrochemical studies of complexes 1–4 show quasireversible redox behavior corresponding to the Cu(I)/Cu(II) couple. Room temperature luminescence is observed for all four complexes. These complexes proved to be effective catalysts for the Sonogashira coupling of terminal alkynes with aryl halides at 90?°C.
Synthesis and spectral properties of novel iminophosphoranes
Fang, Jing-Kun,Xu, Zhimin,Sun, Tengxiao,Fang, Yu,Yin, Zhengxi,Wang, Shijun
, p. 1229 - 1234 (2016)
Three new iminophosphoranes coded as FPZ1 (Ph–C≡C–C6H4–N = PPh3), FPZ2 (Ph–N = P(C6H4–C≡C–Ph)3) and FPZ3 (Ph–C≡C–C6H4–N = P(C6H4–C≡C–Ph)3) were designed and synthesized by introducing different numbers of phenylene acetylene units to FPZ0 (Ph–N = PPh3). The effect of structural modification was studied in detail analyzing the absorption spectra, the emission spectra, and the distributions of the electron density. The absorption spectra of the new iminophosphoranes are shown to be a linear combination of the spectra of each part by the artificial combinatorial absorption spectrum, which coincides with the real one. Most probably the individual parts can’t conjugate due to the tetrahedral structure. The probably formed excimer of FPZ0 and FPZ1 causes in their solid emission spectra an obvious bathochromic shift as compared to that of FPZ2 and FPZ3. The melting point data also showed that long branches of FPZ2 and FPZ3 will attenuate the interactions between the molecules. The results of quantum chemical calculations show that the electronic density in the HOMO of FPZ1, FPZ2, and FPZ3 is delocalized over the iminoaryl moieties. The electron density in the LUMO is delocalized over the triaryl phosphine moieties, but only concentrated on two branches, which directly determines the main direction of intramolecular charge transfer.
Pd(II)–acylthiourea complex and its immobilized counterpart catalyzed condensation of phenylacetylene with aryl halides
Sindhuja,Vasanthakumar,Karvembu
, (2020)
New Pd(II) complex, trans-[PdCl2L2] (1) (L = N-carbamothioylthiophene-2-carboxamide), was prepared and characterized. Its heterogeneous counterpart, trans-[PdCl2(L-SNPs)2] (2) (L-SNPs = ligand immobilized on silica nanoparticles), was also prepared through covalent modification of the ligand using silica nanoparticles and characterized. Both 1 and 2 were exploited for their catalytic activity towards condensation of phenylacetylene with aryl halides. The complexes exhibited good activity when aryl halide bears I? or Br? group. Further, catalyst 2 can be reused for four cycles.
DNA-Decorated, Helically Twisted Nanoribbons: A Scaffold for the Fabrication of One-Dimensional, Chiral, Plasmonic Nanostructures
Golla, Murali,Albert, Shine K.,Atchimnaidu, Siriki,Perumal, Devanathan,Krishnan, Nithiyanandan,Varghese, Reji
, p. 3865 - 3869 (2019)
Crafting of chiral plasmonic nanostructures is extremely important and challenging. DNA-directed organization of nanoparticle on a chiral template is the most appealing strategy for this purpose. Herein, we report a supramolecular approach for the design of DNA-decorated, helically twisted nanoribbons through the amphiphilicity-driven self-assembly of a new class of amphiphiles derived from DNA and hexaphenylbenzene (HPB). The ribbons are self-assembled in a lamellar fashion through the hydrophobic interactions of HPB. The transfer of molecular chirality of ssDNA into the HPB core results in the bias of one of the chiral propeller conformations for HPB and induces a helical twist into the lamellar packing, and leads to the formation of DNA-wrapped nanoribbons with M-helicity. The potential of the ribbon to act as a reversible template for the 1D chiral organization of plasmonic nanomaterials through DNA hybridization is demonstrated.
An efficient and recyclable magnetic-nanoparticle-supported palladium catalyst for the suzuki coupling reactions of organoboronic acids with alkynyl bromides
Zhang, Xiuli,Li, Pinhua,Ji, Yong,Zhang, Lei,Wang, Lei
, p. 2975 - 2983 (2011)
A highly active, air- and moisture-stable and easily recoverable magnetic-nanoparticle-supported palladium catalyst has been developed for the Suzuki cross-coupling reaction of organoboron derivatives with alkynyl bromides. In the presence of palladium catalyst (0.5 mol%), organoboron derivatives including aromatic and aliphatic boronic acids, potassium aryltrifluoroborates, and sodium tetraphenylborate reacted smoothly with 1-bromo-2-substituted acetylenes to generate the corresponding cross-coupling products in good to excellent yields in ethanol. In addition, it is possible to recover and reuse the supported palladium catalyst at least 16 times without significant loss of its catalytic activity. Georg Thieme Verlag Stuttgart - New York.
DABCO-functionalized silica-copper(i) complex: A novel and recyclable heterogeneous nanocatalyst for palladium-free Sonogashira cross-coupling reactions
Hajipour, Abdol Reza,Hosseini, Seyed Mostafa,Mohammadsaleh, Fatemeh
, p. 6939 - 6945 (2016)
A DABCO-functionalized silica supported copper(i)-based nanocatalyst was successfully prepared using a novel and simple route, in which the DABCO as an important functional entity acts as both a stable linker and an excellent chelator. Initially, Cu(ii) i
Microwave irradiated solventless Sonogashira reaction on nickel(0) powder doped KF/Al2O3
Wang, Min,Li, Pinhua,Wang, Lei
, p. 2803 - 2812 (2004)
A microwave irradiated solventless Sonogashira coupling reaction catalyzed by nanosize nickel(0) powder on potassium fluoride-alumina mixture has been developed. Terminal alkynes couple with aryl, alkenyl iodide, and aryl bromide in the presence of cuprou
A novel imidazolium-supported palladium-chloroglycine complex: Copper- and solvent-free high-turnover catalysts for the Sonogashira coupling reaction
Karthikeyan, Parasuraman,Muskawar, Prashant Narayan,Aswar, Sachin Arunrao,Bhagat, Pundlik Rambhau,Sythana, Suresh Kumar
, p. 562 - 569,8 (2012)
A novel, effective 1-glycyl-3-methyl imidazolium chloride-palladium(II) complex ([Gmim]Cl-Pd(II)) was synthesized and studied as an organocatalyst for the Sonogashira coupling reaction under solvent-free conditions at 25 °C. The hydrophobic group on amino acid favors reagent diffusion toward the chloroglycine moiety, increasing the catalytic activity of supported palladium complex. By this protocol, different aryl halides (Cl, Br and I) were reacted with phenylacetylene in good to excellent yields with turnover number 8.0 × 102 to 9.6 × 102. The catalyst was recycled for the reaction of bromobenzene with phenylacetylene for eight runs without appreciable loss of its catalytic activity and negligible metal leaching. Copyright
Palladium(II)eSchiff base complex supported on multi-walled carbon nanotubes: A heterogeneous and reusable catalyst in the Suzukie Miyaura and copper-free SonogashiraeHagihara reactions
Navidi, Mozhgan,Rezaei, Nasrin,Movassagh, Barahman
, p. 63 - 69 (2013)
The air-moisture stable and recyclable palladium(II) Schiff base complex anchored to multi-walled carbon nanotubes (PdeSchiff base@MWCNTs) behaves as a very efficient heterogeneous catalyst in the SuzukieMiyaura coupling of arylboronic acids and aryl halides, and the SonogashiraeHagihara reaction of aryl iodides and terminal alkynes in aqueous media to afford the corresponding CeC couplings in high yields.
Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions
Niknam, Esmaeil,Panahi, Farhad,Khalafi-Nezhad, Ali
supporting information, (2021/01/12)
A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.
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.]
Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation to Achieve Isoquinoline Synthesis
Cui, Hong,Bai, Jinku,Ai, Tianyu,Zhan, Ye,Li, Guanzhong,Rao, Honghua
supporting information, p. 4023 - 4028 (2021/05/26)
We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.
