16619-61-7Relevant academic research and scientific papers
Acetylene and terminal alkyne complexes of copper(i) supported by fluorinated pyrazolates: Syntheses, structures, and transformations
Parasar, Devaborniny,Ponduru, Tharun T.,Noonikara-Poyil, Anurag,Jayaratna, Naleen B.,Dias, H.V. Rasika
, p. 15782 - 15794 (2019)
Trinuclear {μ-[3,5-(CF3)2Pz]Cu}3 reacts with acetylene to produce the 2:1 copper(i) acetylene complex, Cu4(μ-[3,5-(CF3)2Pz])4(μ-HCCH)2. Related Cu4(μ-[4-Br-3,5-(CF3)2Pz])4(μ-HCCH)2 and Cu4(μ-[4-Cl-3,5-(CF3)2Pz])4(μ-HCCH)2 have also been isolated using the corresponding copper(i) pyrazolate and acetylene. The 1:1 adducts Cu2(μ-[3,5-(CF3)2Pz])2(HCCH)2 and Cu2(μ-[4-Br-3,5-(CF3)2Pz])2(HCCH)2 are significantly less stable to the acetylene loss and can be observed in solution at low temperatures under excess acetylene. The X-ray crystal structures of 2:1 and 1:1 complexes, Cu4(μ-[3,5-(CF3)2Pz])4(μ-HCCH)2 and Cu2(μ-[4-Br-3,5-(CF3)2Pz])2(HCCH)2 are reported. Raman data show a reduction in CC stretching frequency by about ～340 and ～163 cm-1 in the 2:1 and 1:1 Cu(i)/acetylene complexes, respectively, from that of the free acetylene. Copper(i) pyrazolate complexes of the terminal alkynes, phenylacetylene, 1,8-nonadiyne, and 1,7-octadiyne are also reported. They form adducts involving one copper atom on each alkyne moiety. The {μ-[3,5-(CF3)2Pz]Cu}3 is also a very versatile and competent catalyst for alkyne transformations as evident from its ability to catalyze the alkyne C(sp)-H bond carboxylation chemistry with CO2, azide-alkyne cycloadditions leading to 1,2,3-triazoles including the use of acetylene itself as a substrate, and thiol addition to phenylacetylene affording vinyl sulfides.
Regio- and stereoselective synthesis of vinyl sulfides via PhSeBr-catalyzed hydrothiolation of alkynes
Manarin, Flávia,Roehrs, Juliano A.,Prigol, Marina,Alves, Diego,Nogueira, Cristina W.,Zeni, Gilson
, p. 4805 - 4808 (2007)
We present here a simple and mild method of hydrothiolation of internal and terminal alkynes under PhSeBr-catalyzed reaction in the absence of solvent at room temperature. The reaction tolerates a wide variety of substituents on thiol, and provides the co
Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction
Pan, Yi,Wang, Yang,Wang, Yi,Zhang, Feng
, (2022/02/16)
This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
Sodium iodide-mediated synthesis of vinyl sulfides and vinyl sulfones with solvent-controlled chemical selectivity
Liu, Congrong,Wu, Gongde,Xu, Jin
, p. 35156 - 35160 (2021/11/30)
Vinyl sulfides and vinyl sulfones are ubiquitous structures in organic chemistry because of their presence in natural and biologically active compounds and are very frequently encountered structural motifs in organic synthesis. Herein we report an efficie
Gem-Heterosubstituted (stannyl)methylsilanes as synthetic equivalents of functionalized α-stannyl(methyl) anions
Tanini, Damiano,Nocentini, Tiziano,Capperucci, Antonella
, p. 99 - 113 (2020/02/13)
α-Heterosubstituted silyl derivatives, such as phenylthio-, phenylseleno- and benzotriazolyl-stannyl silanes, react with aldehydes under tetra-n-butylammonium fluoride (TBAF) catalysis, leading to α-substituted-βhydroxy stannanes, able to behave as precursors of Z- and E-olefins, generated by deoxystannylation. This reactivity shows the capability of such heterosubstituted silanes to act as masked carbanions through a mild functionalization of the carbon-silicon bond.
Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries
Lin, Shishi,Lies, Shane D.,Gravatt, Christopher S.,Yoon, Tehshik P.
supporting information, p. 368 - 371 (2017/04/21)
The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach constitutes a novel oxidative “redox auxiliary” strategy that offers a practical means to circumvent a fundamental thermodynamic limitation facing photoredox reactions.
A Hemilabile and Cooperative N-Donor-Functionalized 1,2,3-Triazol-5-Ylidene Ligand for Alkyne Hydrothiolation Reactions
Strydom, Ian,Guisado-Barrios, Gregorio,Fernández, Israel,Liles, David C.,Peris, Eduardo,Bezuidenhout, Daniela I.
supporting information, p. 1393 - 1401 (2017/02/05)
A series of novel cationic and neutral Rh complexes with an N-donor-functionalized 1,2,3-triazol-5-ylidene (TRZ) ligand (in which the pendant N donor is NHBoc, NH2, or NMe2) is described. The catalytic activity of these complexes was
Highly regioselective double hydrothiolation of terminal acetylenes with thiols catalyzed by palladium diacetate
Mitamura, Takenori,Daitou, Masayuki,Nomoto, Akihiro,Ogawa, Akiya
body text, p. 413 - 415 (2011/05/16)
Treatment of terminal acetylenes 1 with two equivalents of thiols 2 in the presence of Pd(OAc)2 catalyst and H2O causes regioselective double hydrothiolation of 1, leading to the corresponding dithioketals 3 in moderate to good yields.
Native silica nanoparticle catalyzed anti-Markovnikov addition of thiols to inactivated alkenes and alkynes: a new route to linear and vinyl thioethers
Banerjee, Subhash,Das, Jayanta,Santra, Swadeshmukul
scheme or table, p. 124 - 127 (2009/04/14)
A new route for the synthesis of linear and vinyl thioethers has been demonstrated using bare silica nanoparticle as catalyst at room temperature under solvent-free conditions. The catalyst can be reused up to six times without loss of catalytic activity.
Mild Copper(I) iodide/β-keto ester catalyzed coupling reactions of styryl bromides with phenols, thiophenols, and imidazoles
Bao, Weiliang,Liu, Yunyun,Lv, Xin
experimental part, p. 1911 - 1917 (2009/04/04)
An efficient and mild vinylation of O-, S-, and N-nucleophiles is reported. Copper(I) iodide/ethyl 2-oxocyclohexanecarboxylate is used as the catalytic system. The protocol tolerates a broad range of functional groups on the substrates, and gives the corr
