2735-14-0Relevant articles and documents
Probing delocalisation across highly ethynylated mono and dinuclear Pt(II) tethers containing nitrogroups and organic models as redox active probes: X-ray crystal structure of trans-[Pt(CC-C6H4NO2) 2(PPh3
Ravera, Mauro,D'Amato, Rosaria,Guerri, Annalisa
, p. 2376 - 2380 (2005)
The electrochemical study on Pt(II) organometallic and organic ethynylated compounds bearing nitro substituents in the phenyl groups has been performed, demonstrating that the presence of severe chemical irreversibility accompanying the electron transfer,
A new access to tri(1-naphthyl)phosphine and its catalytically active palladacycles and luminescent Cu(I) complex
Artem'ev, Alexander V.,Kuimov, Vladimir A.,Matveeva, Elena A.,Bagryanskaya, Irina Yu.,Govdi, Anastasia I.,Vasilevsky, Sergey F.,Rakhmanova, Mariana I.,Samultsev, Dmitry O.,Gusarova, Nina K.,Trofimov, Boris A.
, p. 94 - 97 (2017)
New approach to synthesis of tri(1-naphthyl)phosphine (Np3P) and its application for design of new Pd(II) and Cu(I) complexes are reported. This phosphine has been prepared in 32% yield through exhaustive P–H arylation of РН3 with 1-chloronaphthalene in the superbasic t-BuOK/DMSO system at 70 °C. The Np3P was found to readily reacts with chloro-bridged dimers, [(κ2-C,N)Pd(μ-Cl)]2 (κ2-C,N = PhCH2NMe2 (2a) or FcCH2NMe2 (2b), to give new mononuclear palladacycles [(κ2-C,N)Pd(Np3P)Cl] (3, 4), in which metal has a square-planar geometry. These complexes show good catalytic activity in the Sonogashira reaction under low catalyst loadings (2 mol% Pd) and relatively mild conditions. We also synthesized and characterized first Cu(I) complex with Np3P, namely, [Cu(phen)(Np3P)I], that exhibits red emission (λmax = 650 nm) at room temperature.
Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System
Yu, Wentao,Zhu, Baiyao,Shi, Fuxing,Zhou, Peiqi,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 1313 - 1322 (2020/12/01)
A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.
Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations
Prusty, Namrata,Banjare, Shyam Kumar,Mohanty, Smruti Ranjan,Nanda, Tanmayee,Yadav, Komal,Ravikumar, Ponneri C.
supporting information, p. 9041 - 9046 (2021/11/30)
Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.
Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction
Ghodsinia, Sara S. E.,Akhlaghinia, Batool,Jahanshahi, Roya
, p. 3217 - 3244 (2021/05/17)
Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es
Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles
Sattler, Lars E.,Hilt, Gerhard
supporting information, p. 605 - 608 (2020/12/07)
The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.
Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling
Deol, Harnimarta,Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
, p. 11080 - 11093 (2020/10/12)
With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.
Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines
Niesobski, Patrik,Martínez, Ivette Santana,Kustosz, Sebastian,Müller, Thomas J. J.
supporting information, p. 5214 - 5218 (2019/07/31)
We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.
Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters
Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
supporting information, p. 2514 - 2517 (2019/04/30)
Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.
Pd-Catalyzed Alkyne Insertion/C-H Activation/[4 + 2] Carboannulation of Alkenes to the Synthesis of Polycyclics
Guo, Songjin,Li, Panpan,Guan, Zhe,Cai, Libo,Chen, Siwei,Lin, Aijun,Yao, Hequan
supporting information, p. 921 - 925 (2019/05/16)
An unprecedented Pd-catalyzed alkyne insertion/C-H activation/intramolecular [4 + 2] carboannulation of alkenes has been reported. In this transformation, the C-H activation was triggered by an in situ generated alkenylpalladium species via the Pd-catalyzed cross-coupling reaction of aryl iodides and alkynes. Subsequently, the resulting five-membered C, C-palladacycle intermediates were added across the alkenes, providing a unique approach to access diversified polycyclics in good efficiency. Two new rings and three C-C bonds were formed in one pot.
