10537-63-0Relevant articles and documents
Nickel-catalysed cross-coupling reactions of aryl halides with organostannanes
Shirakawa, Eiji,Yamasaki, Kenji,Hiyama, Tamejiro
, p. 2449 - 2450 (1997)
A triphenylphosphine-nickel complex is found to be an active catalyst for the cross-coupling reactions of various types of aryl halides, including unactivated aryl chlorides, with alkynyl-, alkenyl- and allyl-stannanes to give the corresponding coupled products in high yields.
Flavylium-supported poly(N -isopropylacrylamide): A class of multistimuli responsive polymer
Jordao, Noemi,Gavara, Raquel,Parola, A. Jorge
, p. 9055 - 9063 (2013)
A new multistimuli responsive polymer was prepared by means of the free-radical copolymerization of N-isopropylacrylamide and a vinyl flavylium derivative. The polymer shows response to temperature (conferred by the N-isopropylacrylamide units) and pH and light stimuli (conferred by the flavylium moieties). The polymer follows the typical pH dependent network of chemical reactions of flavylium compounds in water that was studied by means of UV-vis spectroscopy and stationary fluorescence emission. Regarding the temperature response, the presence of the flavylium cation in the polymeric chains reduces the LCST, and it is possible to take advantage of this effect to photo-collapse partially the polymer by irradiating the system in defined ranges of pH and temperature.
Evaluation of Potential Safety Hazards Associated with the Suzuki-Miyaura Cross-Coupling of Aryl Bromides with Vinylboron Species
Yang, Qiang,Canturk, Belgin,Gray, Kaitlyn,McCusker, Elizabeth,Sheng, Min,Li, Fangzheng
, p. 351 - 359 (2018)
The potential safety hazards associated with the Suzuki-Miyaura cross-coupling of aryl bromides with vinylboron species were evaluated. In the Suzuki-Miyaura cross-coupling of 1-bromo-3-(trifluoromethyl)benzene with potassium vinyltrifluoroborate in the presence of potassium carbonate (K2CO3) in 9:1 dimethyl sulfoxide (DMSO)/water at 80 °C, the thermal profile revealed a significant exotherm upon the addition of catalytic 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride [Pd(dppf)Cl2]. Further investigations indicated that the exotherm was consistently higher and the reactions were faster in the studied aqueous systems compared to anhydrous conditions. Although under anhydrous conditions the exotherms were comparable among the studied cases, the rate of the exotherm was highly dependent on the choice of aryl electrophile, solvent, base, catalyst, as well as vinylboron species. In many of the studied cases the maximum temperature of a synthesis reaction (MTSR) was considerably higher than the boiling point of the solvent and/or the onset temperature of the DMSO decomposition, indicating that in the absence of active cooling the system could quickly exceed the boiling point of the solvent or trigger the decomposition of the reaction mixture to result in a runaway reaction.
Preparation of nonsymmetrically substituted stilbenes in a one-pot two-step Heck strategy using ethene as a reagent
Kormos, Chad M.,Leadbeater, Nicholas E.
, p. 3854 - 3858 (2008)
(Chemical Equation Presented) We present here a strategy for the preparation of nonsymmetrically substituted stilbenes using a one-pot two-step double Heck strategy. First a protocol is developed for the selective preparation of a range of styrenes using ethene as the alkene coupling partner. Then conditions are found for the effective coupling of the styrenes with aryl halides using a 1:1 stoichiometric ratio of the two components. The use of the microwave apparatus to perform the reactions offers a convenient method for synthesis as well as for safely, easily, and accurately loading vessels with gaseous reagents.
The first fluoride-free Hiyama reaction of vinylsiloxanes promoted by sodium hydroxide in water
Alacid, Emilio,Najera, Carmen
, p. 2085 - 2091 (2006)
The first cross-coupling reaction between vinylalkoxysilanes and aryl bromides or chlorides promoted by aqueous sodium hydroxide under fluoride-free conditions to provide styrenes is reported. The reaction is catalyzed by palladium(II) acetate or a 4-hydroxyacetophenone oxime-derived palladacycle either under thermal or microwave heating at 120°C with low catalyst loading (0.01-1 mol% of palladium) in the presence of tetra-n-butylammonium bromide (TBAB) as additive in air. In the case of styryltriethoxysilane, the coupling with aryl or vinyl bromides takes place stereospecifically to give the corresponding stilbenes or dienes, respectively. These mild and simple reaction conditions prevent undesirable polymerization of the products.
Stereoselective synthesis of (E)- and (Z)-triethoxy(vinyl-d 2)silanes by hydrosilylation of acetylene-d 2
Gordillo, Alvaro,Forigua, Johan,Lopez-Mardomingo, Carmen,De Jesus, Ernesto
, p. 352 - 355 (2011)
The hydrosilylation of deuterated acetylene with triethoxysilane can be directed to the synthesis of either cis or trans triethoxy(vinyl-d 2)silanes by an appropriate choice of metal catalyst. In addition, we have demonstrated the viability of designing hydrosilylation-arylation sequential processes in which acetylene can be converted into styrenes or stilbenes using the same Pd catalyst for both reactions.
The first general method for Stille cross-couplings of aryl chlorides
Littke, Adam F.,Fu, Gregory C.
, p. 2411 - 2413 (1999)
A 'one-two punch' comprising two commercially available reagents, PtBu3 and CsF, provides a practical and general solution for a long-standing limitation of the Stille reaction - the inability to couple inexpensive and readily available aryl chlorides [Eq. (1); R1 = OMe, NH2, o-Me, etc.; R = vinyl, allyl, Ph, Bu, etc.].
Vinylation of aryl bromides using an inexpensive vinylpolysiloxane
Denmark, Scott E.,Butler, Christopher R.
, p. 63 - 66 (2006)
(Chemical Equation Presented) A mild and general method for the palladium-catalyzed vinylation of aryl bromides has been developed. The use of tetrabutylammonium fluoride (TBAF) as the activator and an inexpensive and nontoxic vinyl donor, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane (D4V, 1), allows for a general and high-yielding preparation of substituted styrenes.
Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates
Grasa, Gabriela A.,Nolan, Steven P.
, p. 119 - 120 (2001)
(equation presented) A Pd(OAc)2/imidazolium chloride system has been used to mediate the catalytic cross-coupling of aryl halides with organostannanes. The imidazolium salt IPr·HCl (IPr = 1,3-bis(2,6-diisopropylphenyl) imidazol-2-ylidene) in combination with TBAF (nBu4NF) was found to be most effective for the cross-coupling of aryl bromides and electron-deficient aryl chlorides with aryl and vinyl stannanes.
Stille coupling reactions catalysed by a polymer supported palladium complex
Dell'Anna, Maria Michela,Lofù, Antonio,Mastrorilli, Piero,Mucciante, Vittoria,Nobile, Cosimo Francesco
, p. 131 - 137 (2006)
The coupling between aryl iodides and bromides with organostannanes (Stille reaction) has been investigated in the presence of a polymer supported palladium catalyst. The reaction could be performed in air without any activating ligand and with non-dried solvents. The catalyst, which acts by releasing controlled amounts of soluble active species, could be recycled several times in the coupling between Sn(CH3)4 or nBu3SnPh with iodoarenes or activated bromoarenes.
