92-66-0Relevant articles and documents
Acceleration of Suzuki coupling reactions by abundant and non-toxic salt particles
Zhang, Binbin,Song, Jinliang,Liu, Huizhen,Shi, Jinghua,Ma, Jun,Fan, Honglei,Wang, Weitao,Zhang, Peng,Han, Buxing
, p. 1198 - 1201 (2014)
Enhancement of reaction efficiency using non-toxic, abundant, and cheap additives is an interesting topic in green chemistry. In this paper, we report the first work to study the effect of salt particles on organic reactions in different solvents, in which the salts were not soluble, and it was discovered that NaCl, KCl, Na2SO4 and K2SO4 particles could considerably accelerate Suzuki coupling reactions catalyzed by the Pd nanocatalysts. X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared spectroscopy (FT-IR) studies indicated that there exist strong interactions between the salts and the catalyst (Pd) and between the salts and the reactants, which are important reasons for the synergistic effect of the catalyst and the salts. The application of salt particles suspended in organic reaction systems may become a useful strategy to develop new and green reaction routes.
Transfer of heterocyclic carbene ligands from chromium to gold, palladium and platinum
Kessler, Florian,Szesni, Normen,Maa?, Chaya,Hohberger, Christiane,Weibert, Bernhard,Fischer, Helmut
, p. 3005 - 3018 (2007)
The reaction of pentacarbonyl(pyrazolin-3-ylidene)chromium complexes, {A figure is presented} (2a-c) (R = Ph (a), C6H4NMe2-4 (b); (C5H4)FeCp (c)), with [AuCl(SMe2)], H[AuCl4], [PdCl2(NCPh)2] and [PtCl2(NCPh)2] gives, by transfer of the heterocyclic carbene ligand, new chloro pyrazolin-3-ylidene complexes of gold(I) and gold(III), dichloro bis(pyrazolin-3-ylidene) palladium and dichloro bis(pyrazolin-3-ylidene) platinum in high yield. The chloride ligand in {A figure is presented} (Fc = (C5H4)FeCp) is readily displaced by trifluoroacetate. The analogous substitution of iodide for the chloride ligands in {A figure is presented} (M = Pd, Pt) give the corresponding diiodo complexes although in a much slower reaction. In contrast, the reaction of silver trifluoroacetate with {A figure is presented} affords a binuclear Pd-Ag complex containing two pyrazolin-3-ylidene and three trifluoroacetate ligands two of whom occupy bridging positions between Pd and Ag. The reactions of the pyrazolidin-3-ylidene complex {A figure is presented} (R = C6H4NMe2-4) with [AuCl(SMe2)] and [PdCl2(NCPh)2] yield chloro pyrazolidin-3-ylidene gold and dichloro bis(pyrazolidin-3-ylidene) palladium complexes. The related dichloro bis(tetrahydropyrimidin-4-ylidene) palladium complex is formed in the reaction of {A figure is presented} with the palladium complex [PdCl2(NCPh)2]. The solid-state structures of several of these heterocyclic carbene complexes including the structure of the binuclear Pd-Ag complex are established by X-ray structure analyses.
Supramolecular Nanotubules as a Catalytic Regulator for Palladium Cations: Applications in Selective Catalysis
Wu, Shanshan,Li, Yongguang,Xie, Siying,Ma, Cong,Lim, Joonwon,Zhao, Jiong,Kim, Dae Seok,Yang, Minyong,Yoon, Doong Ki,Lee, Myongsoo,Kim, Sang Ouk,Huang, Zhegang
, p. 11511 - 11514 (2017)
Despite the recent development of highly efficient and stable metal catalysts, conferral of regulatory characteristics to the catalytic reaction in heterogeneous systems remains a challenge. Novel supramolecular nanotubules were prepared by alternative stacking from trimeric macrocycles, which was found to be able to coordinate with Pd cations. The Pd complexes exhibited a high catalytic performance for C?C coupling reaction. Notably, the tubular catalyst was observed to be controlled by supramolecular reversible assembly and showed superior heterogeneous catalytic activity, which was maintained for a number of cycles or reuse under an aerobic environment. Furthermore, the supramolecular catalyst showed unprecedented selectivity for the multifunctional coupling reaction and was able to serve as a new constructor of asymmetrical compounds.
Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives
Das, Tapas Kumar,Kundu, Mrinalkanti,Mondal, Biswajit,Ghosh, Prasanjit,Das, Sajal
, p. 208 - 218 (2021/12/29)
A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.
Recycling Oryza sativa wastes into poly-imidazolium acetic acid-tagged nanocellulose Schiff base supported Pd nanoparticles for applications in cross-coupling reactions
Elshaarawy, Reda F. M.,Yahya, Rana
, (2021/12/22)
A green and sustainable heterogeneous nanocatalyst for the Suzuki reaction was fabricated by refining rice straw to ionic nanocellulose Schiff base (NCESB) which was employed for bio-reduction of Pd(II) into Pd nanoparticles (Pd NPs) and immobilization of these NPs to fabricate the desired nanocatalyst (NCESB@Pd). The TEM image revealed well-dispersed PdNPs with sizes of 5–23 nm. The new nanocatalyst displayed amazing activity in catalyzing coupling reactions of a wide range of halobenzenes with phenylboronic acid at 50 °C (reaction time 15–60 min) and even at room temperature (reaction time 120 min). The NCESB@Pd nanocatalyst exhibited excellent recyclability (up to five catalytic runs) without a significant loss of its activity or identity. Therefore, the new ionic nanocatalyst may open a new window for a novel generation of ionic low-cost green and highly effective nanocatalysts for organic transformation reactions.
Sterically enhanced 2-iminopyridylpalladium chlorides as recyclable ppm-palladium catalyst for Suzuki–Miyaura coupling in aqueous solution
Lin, Wenhua,Zhang, Liping,Ma, Yanping,Liang, Tongling,Sun, Wen-Hua
, (2021/10/20)
Sterically hindered 2-iminopyridine derivatives and their palladium chlorides complexes are designed and prepared, which efficiently promote the Suzuki–Miyaura coupling (SMC) reaction in aqueous solution. Besides the good to excellent yields and broad substrate scope, these catalysts can be reused for at least four new batches of the substrates. Spontaneous separation of coupling products in the aqueous reaction medium is the additional striking feature of this catalytic process. Furthermore, catalytic performance of palladium complexes bearing the azo-bridged phenyl groups was greatly influenced by the UV irradiation due to the cis/trans photoisomerization of azo unit of the catalysts. In conclusion, titled palladium complexes provide a green, sustainable, cost-effective, and convenient process to synthesize SMC products at multi-gram-scale reaction.
A Photoreactive Iron(II) Complex Luminophore
Argüello Cordero, Miguel A.,Berkefeld, Andreas,Leis, Wolfgang,Lochbrunner, Stefan,Schubert, Hartmut
supporting information, p. 1169 - 1173 (2022/02/05)
Controlling the order and lifetimes of electronically excited states is essential to effective light-to-potential energy conversion by molecular chromophores. This work reports a luminescent and photoreactive iron(II) complex, the first performant group homologue of prototypical sensitizers of ruthenium. Double cyclometalation of a phenylphenanthroline framework at iron(II) favors the population of a triplet metal-to-ligand charge transfer (3MLCT) state as the lowest energy excited state. Near-infrared (NIR) luminescence exhibits a monoexponential decay with τ = 2.4 ns in the solid state and 1 ns in liquid phase. Lifetimes of 14 ns at 77 K are in line with a narrowing of the NIR emission band at λem,max = 1170-1230 nm. Featuring a 3MLCT excited-state redox potential of -2 V vs the ferrocene/ferrocenium couple, the use of the Fe(II) chromophore as a sensitizer for light-driven synthesis is exemplified by the radical cross-coupling of 4-chlorobromobenzene and benzene.
Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold
Medina-Mercado, Ignacio,Porcel, Susana
, (2022/03/15)
A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.
Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
supporting information, p. 1297 - 1300 (2020/12/23)
A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
Anchored PdCl2 on fish scale: an efficient and recyclable catalyst for Suzuki coupling reaction in aqueous media
Yang, Quanlu,Yang, Fawang,Zhang, Ying,Hou, Juanjuan,Li, Jiankun,Cheng, Jinkui,Wu, Shang,Zhan, Huiying,Zhang, Xinghui,Shi, Haixiong
supporting information, (2020/12/25)
PdCl2 anchored on fish scale (FS) complex were intended to a heterogeneous catalyst for ligand-free Suzuki coupling reaction in aqueous media. The catalyst FS-PdCl2 was characterized by FT-IR, powder XRD, XPS and SEM. FS-PdCl2 complex has been successfully implemented for Suzuki coupling reactions of various halogenated aromatics with arylboronic acid to provide the corresponding biaryl compounds under environmentally friendly conditions (40 °C, water solvent). Moreover, the efficient catalyst shows excellent stability and recyclability, and its catalytic activity without any decrease after 8 times consecutive reused.
