101466-85-7Relevant articles and documents
Ruthenium(II)-salen complexes-catalyzed olefination of aldehydes with ethyl diazoacetate
Sun, Wei,Yu, Bingsheng,Kühn, Fritz E.
, p. 1993 - 1996 (2006)
Several salen-ruthenium(II) complexes, which are derived from commercial ligands or simply ethylenediamine, can be successfully applied as catalysts for the olefination of a broad variety of aldehydes. Depending on the electron richness of the applied aldehydes, good to very good olefin yields and high E:Z selectivities are reached at 60 or 80°C reaction temperature with ethyl diazo acetate being the reaction partner. The reaction rate depends on the electron donor capabilities of the aldehydes. Electron poor aldehydes undergo faster reactions than electron rich aldehydes, but both electron rich and bulky aldehydes can be transformed to corresponding olefins in very good yields and high E-selectivity.
Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions
Suárez-Escobedo, Laura,Gotor-Fernández, Vicente
, (2021)
The esterification of cinnamic acid has been deeply investigated using ethanol as nucleophile and Candida antarctica lipase type B (CAL-B) as suitable biocatalyst. Special attention has been paid to the role that the solvent plays in the production of ethyl cinnamate. Therefore, volatile organic solvents and deep eutectic mixtures were employed in order to find optimal reaction conditions. Once that hexane was selected as the solvent of choice, other parameters that affect the enzyme activity were investigated in order to produce ethyl cinnamate with excellent yield. The CAL-B loading, nucleophile equivalents, temperature and reaction time have been identified as key parameters in the enzyme efficiency, and the potential of lipase-catalysed esterification has been finally exploited to produce a series of ethyl esters with different pattern substitutions on the aromatic ring.
A practical catalytic Wittig-type reaction
Huang,Ye,Xia,Tang
, p. 1384 - 1385 (2001)
Soluble PEG-supported telluride 2 was synthesized and found to be an effective catalyst for the catalytic Wittig-type reaction to give a variety of α,β-unsaturated esters in high yields with excellent E-stereoselectivity in the presence of sodium bisulfite as well as triphenyl phosphite.
Gold-catalyzed partial hydrogenation of activated alkynes mediated by triphenylphosphine
Cocoletzi-Xochitiotzi, Ana Patricia,Hernández-Hernández, Miguel,Medina-Mercado, Ignacio,Jiménez-Martínez, Williams De Jesús,Mastranzo, Virginia Maricela,Porcel, Susana
, p. 2379 - 2386 (2020)
Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z -isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.
Pd-porphyrin functionalized ionic liquid-modified mesoporous SBA-15: An efficient and recyclable catalyst for solvent-free Heck reaction
Zhang, Jing,Zhao, Guo-Feng,Popovi?, Zora,Lu, Yong,Liu, Ye
, p. 1648 - 1653 (2010)
The Pd-porphyrin functionalized ionic liquid could be covalently anchored in the channels of mesoporous SBA-15 through ion-pair electrostatic interaction between imidazolium-cationic and Pd-porphyrin-anionic moieties. Such modified SBA-15 materials were prepared successfully via a post-synthesis (surface sol-gel polymerization) or a one-pot sol-gel procedure, which were characterized by powder X-ray diffraction, UV-visible spectroscopy, Fourier transform infrared spectroscopy, N2 sorption, elemental analysis, and transmission electron microscopy. The modified SBA-15 materials are efficient and recyclable catalysts for cross-coupling of aryl iodides or activated aryl bromides with ethyl acrylate without activity loss and Pd leaching even after 9 runs.
Surfactant-free synthesis of palladium nanoclusters for their use in catalytic cross-coupling reactions
Hyotanishi, Megumi,Isomura, Yuto,Yamamoto, Hiroko,Kawasaki, Hideya,Obora, Yasushi
, p. 5750 - 5752 (2011)
Surfactant-free Pd nanoclusters (Pd NCs) (size: 1-1.5 nm) showed high catalytic activity in the Suzuki-Miyaura cross-coupling and Mizoroki-Heck reactions. The Pd NCs had a high turnover number, up to 6.0 × 10 8, which can be recycled at least five times without loss of catalytic activity.
Silica-coated nano-Fe3O4-supported iminopyridine palladium complex as an active, phosphine-free and magnetically separable catalyst for Heck reactions
Zhang, Qiang,Zhao, Xin,Wei, Huai-Xin,Li, Ji-Hang,Luo, Jun
, (2017)
A novel magnetic nanoparticle-supported iminopyridine palladium complex was successfully prepared by attaching palladium acetate to iminopyridine ligand-functionalized silica-coated nano-Fe3O4. The as-prepared catalyst was well characterized and was evaluated in Heck reactions in terms of activity and recyclability. It was found to be highly efficient for the reactions of various aryl iodides and aryl bromides having electron-withdrawing groups with olefins under phosphine-free and inert atmosphere-free conditions. Moreover, the catalyst could be conveniently recovered using an external magnet, and the recyclability was influenced by the base in the Heck reaction. The catalyst could be reused at least six times with no significant loss in activity when triethylamine acted as the base.
Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
Yamamoto, Yuki,Kawaguchi, Shin-Ichi,Nishimura, Misaki,Sato, Yuki,Shimada, Yoshihisa,Tabuchi, Akihiro,Nomoto, Akihiro,Ogawa, Akiya
, p. 14684 - 14696 (2020)
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.
Stereospecific preparation of ethyl (E) and (Z)-3-aryl-3-phenylpropenoates by Heck reaction
Moreno-Manas, Marcial,Perez, Montserrat,Pleixats, Roser
, p. 7449 - 7452 (1996)
Ethyl cinnamate reacts with several para-substituted aryl iodides under Jeffery-Larock conditions (Pd(OAc)2, NaHCO3, n-Bu4NBr, DMF, Δ) to give ethyl (E)-3-aryl-3-phenylpropenoates as major compounds. The reaction of para-substituted ethyl cinnamates with iodobenzene under analogous conditions affords the corresponding Z isomers. The initially stereodefined alkene formed under Heck conditions undergoes a slow isomerization.
Functionalized ionic liquid as an efficient and recyclable reaction medium for phosphine-free palladium-catalyzed heck reaction
Zhou, Li,Wang, Lei
, p. 2653 - 2658 (2006)
A functionalized ionic liquid, 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate ([HEmim][BF4]), was found to be as an efficient and recyclable reaction medium for palladium-catalyzed Heck reaction. The olefination of iodoarenes and bromoarenes with olefins generated the corresponding products in good to excellent yields under phosphine-free reaction conditions. The reaction involved the use of [HEmim][BF4] as the solvent, potassium phosphate as the base, and palladium acetate as the catalyst. In addition, palladium and ionic liquid could be recovered and recycled for six consecutive trials without significant loss of its reactivity. Georg Thieme Verlag Stuttgart.
Asymmetric Synthesis of Functionalized 9-Methyldecalins Using a Diphenylprolinol-Silyl-Ether-Mediated Domino Michael/Aldol Reaction
Hayashi, Yujiro,Salazar, Hugo A.,Koshino, Seitaro
supporting information, p. 6654 - 6658 (2021/09/11)
Substituted 9-methyldecalin derivatives containing an all carbon quaternary chiral center were synthesized with excellent enantioselectivity via an organocatalyst-mediated domino reaction. The first reaction is a diphenylprolinol silyl ether-mediated Michael reaction, and the second reaction is an intramolecular aldol reaction. The enantiomerically pure catalyst is involved in both reactions.
Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents
Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath
, p. 8806 - 8813 (2021/05/26)
We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.
