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.
Palladium-catalyzed cross-coupling reaction of alkenyldimethyl(2-pyridyl)silanes with organic halides: Complete switch from the carbometalation pathway to the transmetalation pathway [13]
Itami,Nokami,Yoshida
, p. 5600 - 5601 (2001)
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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.
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.].
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.
Cross-coupling of vinylpolysiloxanes with aryl iodides
Denmark, Scott E.,Wang, Zhigang
, p. 372 - 375 (2001)
Commercially available vinylpolysiloxane (1) rapidly undergoes cross-coupling reactions with aryl and alkenyl iodides in the presence of tetrabutylammonium fluoride (two to three equivalents) and Pd(dba)2 (1-5 mol%) at room temperature to affor
Tertiary arsine ligands for the Stille coupling reaction
Chishiro, Akane,Imoto, Hiroaki,Inaba, Ryoto,Konishi, Masafumi,Naka, Kensuke,Yumura, Takashi
, p. 95 - 103 (2021/12/27)
The Stille coupling reaction is one of the most important coupling reactions. It is well known that the triphenylarsine ligand can accelerate the reaction rate of Stille coupling. However, other arsine ligands have never been investigated for the Stille c
The Stereoselective Oxidation of para-Substituted Benzenes by a Cytochrome P450 Biocatalyst
Chao, Rebecca R.,Lau, Ian C.-K.,Coleman, Tom,Churchman, Luke R.,Child, Stella A.,Lee, Joel H. Z.,Bruning, John B.,De Voss, James J.,Bell, Stephen G.
supporting information, p. 14765 - 14777 (2021/09/14)
The serine 244 to aspartate (S244D) variant of the cytochrome P450 enzyme CYP199A4 was used to expand its substrate range beyond benzoic acids. Substrates, in which the carboxylate group of the benzoic acid moiety is replaced were oxidised with high activity by the S244D mutant (product formation rates >60 nmol.(nmol-CYP)?1.min?1) and with total turnover numbers of up to 20,000. Ethyl α-hydroxylation was more rapid than methyl oxidation, styrene epoxidation and S-oxidation. The S244D mutant catalysed the ethyl hydroxylation, epoxidation and sulfoxidation reactions with an excess of one stereoisomer (in some instances up to >98 %). The crystal structure of 4-methoxybenzoic acid-bound CYP199A4 S244D showed that the active site architecture and the substrate orientation were similar to that of the WT enzyme. Overall, this work demonstrates that CYP199A4 can catalyse the stereoselective hydroxylation, epoxidation or sulfoxidation of substituted benzene substrates under mild conditions resulting in more sustainable transformations using this heme monooxygenase enzyme.
Zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source
Shen, Guoli,Liu, Haojie,Chen, Jingchao,He, Zhenxiu,Zhou, Yongyun,Wang, Lin,Luo, Yang,Su, Zhimin,Fan, Baomin
supporting information, p. 3601 - 3610 (2021/05/04)
The zinc salt-catalyzed reduction of α-aryl imino esters, diketones and phenylacetylenes with water as hydrogen source and zinc as reductant was successfully conducted. The presented method provides a low-cost, environmentally friendly and practical preparation of α-aryl amino esters, α-hydroxyketones and phenylethylenes. By using D2O as deuterium source, the corresponding products were obtained in high efficiency with excellent deuterium incorporation rate, which gives a cheap and safe tool for access to valuable deuterium-labelled compounds. This journal is
