103-25-3Relevant articles and documents
Palladium Nanoparticles in Polymers: Catalyst for Alkene Hydrogenation, Carbon-Carbon Cross-Coupling Reactions, and Aerobic Alcohol Oxidation
Park, Cheon Min,Kwon, Min Serk,Park, Jaiwook
, p. 3790 - 3794 (2006)
A new recyclable palladium catalyst was synthesized by a simple procedure from readily available reagents, which is composed of palladium nanoparticles dispersed in an organic polymer. This catalyst is robust, and highly active in many organic transformations including alkene and alkyne hydrogenation, carbon-carbon cross-coupling reactions, and aerobic alcohol oxidation.
Continuous-Flow microreactor Chemistry under High-Temperature/pressure
Razzaq, Tahseen,Glasnov, Toma N.,Kappe, C. Oliver
, p. 1321 - 1325 (2009)
High-temperature organic synthesis can be performed under continuous-flow conditions in a stainless steel microtubular flow reactor capable of achieving temperatures of 350 °C and 200 bar. Under these extreme experimental environments transformations normally performed in a high-boiling solvent at reflux temperature - or under sealed-vessel microwave conditions - can be readily converted to a flow regime by using lower boiling solvents in or near their supercritical state. Wiley-VCH Verlag GmbH & Co, KGaA.
Highly regioselective rhodium-catalysed hydroformylation of unsaturated Esters: The first practical method for quaternary selective carbonylation
Clarke, Matthew L.,Roff, Geoffrey J.
, p. 7978 - 7986 (2006)
Highly regioselective hydroformylation of unsaturated esters can be achieved when a highly reactive, ligand-modified, rhodium catalyst is employed near ambient temperatures (15-50°C) and pressures over 30 bar. The use of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane shows distinct advantages over other commonly applied phosphanes in terms of reaction rate, and regio- and chemoselectivity. Hydroformylation of a range 1,1-di- and 1,1,2-trisubstituted unsaturated esters yields quaternary aldehydes that are forbidden products according to Keulemans Rule. The aldehydes can be reductively aminated with molecular hydrogen to give β-amino acid esters in high yield. The overall green chemical process involves converting terminal alkynes into unusual β-amino acid esters with only water generated as an essential byproduct. This catalytic system has also been applied to the hydroformylation of simple 1,2-disubstitued unsaturated esters, which have been hydroformylated with excellent α-selectivity and good chemo-selectivity for the first time.
Practical access to the polymer incarcerated platinum (PI Pt) catalyst and its application to hydrogenation
Miyazaki, Yoji,Hagio, Hiroyuki,Kobayashi, Sh
, p. 2529 - 2531 (2006)
Polymer incarcerated platinum catalysts (PI Pt) were conveniently prepared from PtCl2(COD) or H2PtCl6·6H 2O and styrene copolymers via reduction of the Pt sources with triethylamine, coacervation, and cross-linking. The Pt catalysts have been successfully applied to catalytic hydrogenation including saturation of heterocyclic compounds. The Royal Society of Chemistry 2006.
Highly efficient esterification of carboxylic acids with alcohols by montmorillonite enwrapped titanium as a heterogeneous acid catalyst
Kawabata, Tomonori,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 9205 - 9208 (2003)
Montmorillonite-enwrapped titanium catalyst was found to efficiently promote the esterification of carboxylic acids with alcohols. In comparison to other catalysts reported to date, this heterogeneous catalyst offers a remarkably simple workup procedure, and is reusable without any appreciable loss in its activity and selectivity.
Acylations and Alkylations of an Ester Enolate in High Yield at Room Temperature on Polystyrene Supports
Chang, Young H.,Ford, Warren T.
, p. 3756 - 3758 (1981)
Polymer-bound esters of 3-phenylpropanoic acid are converted to enolates at room temperature and acylated and alkylated in 73-87percent isolated yields with little or no self-condensation of ester.
Hydroesterification of Olefins Catalyzed by Pd(OAc)2 Immobilized on Montmorillonite
Lee, Chul Woo,Alper, Howard
, p. 250 - 252 (1995)
Palladium acetate immobilized on montmorillonite is an efficient catalyst for the hydroesterification of olefins with carbon monoxide and methanol, in the presence of triphenylphosphine and an acid promoter, affording branched chain esters.The reaction is regiospecific for aryl olefins as well as for vinyl benzoate and regioselective for aliphatic olefins.
Asymmetric hydroesterification of styrene using catalysts with planar-chiral ferrocene oxazoline ligands
Wang, Lailai,Kwok, Wai Him,Chan, Albert S. C.,Tu, Tao,Hou, Xuelong,Dai, Lixin
, p. 2291 - 2295 (2003)
Chiral P,N-ferrocene ligands, 1-diphenylphosphino-1′-[(S)-4-isopropyl-2.5-oxazolinyl]-2′-(S p)-(trimethylsilyl)-ferrocene and its diastereomer, and 1-diphenylphosphino-1′-[(S)-4-isopropyl-2.5-oxazolinyl]-2′(S p)-(diphenylphosphino)-ferrocene and its diastereomer were used in the palladium-catalyzed asymmetric hydroesterification of styrene. The role of these ligands, which contain central, axial, and planar chirality, on the stereochemical outcome was investigated. A significant effect of using CuCl2 as a co-catalyst on the reaction was observed. Excellent regioselectivity (b/n >99:1) with low ee (28%) was obtained in the presence of CuCl2; moderate enantioselectivity (64% ee) but low regioselectivity (b/n, 40/60) was obtained in the absence of CuCl2.
Highly active and selective palladium catalyst for hydroesterification of styrene and vinyl acetate promoted by polymeric sulfonic acids
Ooka, Hirohito,Inone, Tsutomu,Itsuno, Shinichi,Tanaka, Masato
, p. 1173 - 1175 (2005)
Highly efficient, selective and recyclable palladium catalyst systems for hydroesterification of styrene and vinyl acetate were realized by using 1,2-bis(di-tert-butylphosphinomethyl)benzene as ligand and polymeric sulfonic acids of limited SO3H loadings as promoter. The Royal Society of Chemistry 2005.
Tris(2,4,6-trimethoxyphenyl)phosphine: Base catalyst in the transformation of α,β-unsaturated aldehydes to saturated carboxylic-acid derivatives
Hayashi, Masahiko,Kawabata, Hirotoshi,Yoshimoto, Kazuya,Tanaka, Takanori
, p. 433 - 445 (2007)
We have focused on the basicity of Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) in organic synthesis. To extend the utility of TTMPP, we examined the reaction of α,β-unsaturated aldehydes with trimethylsilyl cyanide in the presence of TTMPP. Furthermore, to clarify the basic character of TTMPP, we measured 31P NMR of TTMPP and related compounds. First, the reaction of cinnamaldehydes with trimethylsilyl cyanide in the presence of a catalytic amount of TTMPP afforded the corresponding saturated carboxylic acids after hydrolysis with 1M HCl. Treatment of the reaction mixture with alcohols or amines instead of 1M HCl gave the corresponding saturated esters and amides, respectively. As a result of studies of the reaction mechanism, it was revealed that the reaction proceeded via silylcyanation of α,β-unsaturated aldehydes with trimethylsilyl cyanide to produce trimethylsilyl ethers of cyanohydrin and subsequent isomerization that formed α-trimethylsiloxy vinyl cyanides, which were hydrolyzed to give saturated carboxylic acids. Copyright Taylor & Francis Group, LLC.
