33206-62-1Relevant academic research and scientific papers
Cross metathesis of methyl oleate (MO) with terminal, internal olefins by ruthenium catalysts: Factors affecting the efficient MO conversion and the selectivity
Awang, Nor Wahida,Tsutsumi, Ken,Hu?táková, Barbora,Yusoff, Siti Fairus M.,Nomura, Kotohiro,Yamin, Bohari M.
, p. 100925 - 100930 (2016/11/09)
Cross metathesis (CM) reactions of methyl oleate (MO) with cis-4-octene (OC), cis-stilbene (CS) using RuCl2(PCy3)(IMesH2)(CHPh) [IMesH2 = 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene; Cy = cyclohexyl] afforded CM products with high MO conversion and high selectivity under high molar (OC/MO, CS/MO) ratios; CM with cis-1,4-diacetoxy-2-butene also afforded metathesis products with high MO conversion under certain conditions. The efficient CM with allyltrimethylsilane proceeded with high activity, whereas the CM with glycidyl ether, β-pinene, and vanillylidenacetone proceeded with low MO conversion.
General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation
Meng, Guangrong,Szostak, Michal
supporting information, p. 14518 - 14522 (2016/01/25)
Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.
Monodisperse CuB23 nanoparticles grown on graphene as highly efficient catalysts for unactivated alkyl halide Heck coupling and levulinic acid hydrogenation
Fu, Shi Yan,Li, Yuan Zhi,Chu, Wei,Li, Chun,Tong, Dong Ge
, p. 1638 - 1649 (2015/04/27)
Monodisperse CuB23 nanoparticles were successfully grown on graphene by the co-reduction of graphene oxide and Cu(NH3)42+ using KBH4 and with the assistance of solution plasma. Graphene is a powerful dispersion agent and a distinct support for CuB23 nanoparticles. Unexpectedly, we found that the prepared CuB23/graphene catalyst imparts exceedingly high activity to the Heck-type coupling of unactivated alkyl halides with alkenes and the liquid phase hydrogenation of levulinic acid to γ-valerolactone. Additionally, the as-prepared CuB23/graphene also exhibited excellent recyclability during the hydrogenation of levulinic acid. The excellent catalytic performance might be caused by the combined effect of the good dispersion of CuB23 nanoparticles and the interaction between graphene and CuB23 nanoparticles. This not only facilitates electron transfer and mass transport but also improves thermal stability during the catalytic reaction process.
Monodisperse amorphous CuB23 alloy short nanotubes: Novel efficient catalysts for Heck coupling of inactivated alkyl halides and alkenes
Yang, Fan,Fu, Shi Yan,Chu, Wei,Li, Chun,Tong, Dong Ge
, p. 45838 - 45843 (2015/02/19)
Heck-type coupling of inactivated alkyl halides and alkenes, catalyzed by amorphous CuB23 alloy short nanotubes, has been developed. Such couplings occur on the surfaces of nanotubes via a single-electron oxidative reaction. The results indicate that CuB23 nanotubes are efficient catalysts to replace Pd and Ni complexes for such Heck-type coupling. This journal is
Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis
Antonioletti,Bonadies,Ciammaichella,Viglianti
, p. 4644 - 4648 (2008/09/20)
A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.
Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: Assembled complex of palladium and non-cross-linked amphiphilic polymer
Yamada, Yoichi M. A.,Takeda, Koji,Takahashi, Hideyo,Ikegami, Shiro
, p. 7733 - 7741 (2007/10/03)
An assembled insoluble catalyst, PdAS, prepared from palladium ((NH 4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki-Miyaura reaction on three points: (1) The use of 8 × 10 -7 to 5 × 10-4 mol equiv of PdAS afforded the coupling products efficiently after easy workup, with the turnover number reaching up to 1 250 000. (2) The catalyst was reusable many times without loss of catalytic activity. (3) PdAS showed good stability in any reaction medium (i.e., water or aqueous or anhydrous organic solvents). Analytical study of PdAS indicates that the phosphines in 2 coordinate to palladium to form PdCl2(PPh2Ar)2 species.
Heck reactions without salt formation: Aromatic carboxylic anhydrides as arylating agents
Stephan, Massoud S.,Teunissen, Antonius J. J. M.,Verzijl, Gerard K. M.,De Vries, Johannes G.
, p. 662 - 664 (2007/10/03)
Environmentally benign and economical production of arylated olefins can be achieved by a new variant of the Heck reaction in which no halogen salts are formed. The trick is the use of aromatic carboxylic anhydrides 1 as arylating agents. With halide-activated palladium chloride as catalyst, which requires no phosphane ligands, the olefins 2 can be prepared according to Equation (a) in good yields.
Stereochemistry of the olefin formation from anti and syn heterocyclic β-hydroxy sulfones.
Baudin, J. B.,Hareau, G.,Julia, S. A.,Ruel, O.
, p. 336 - 357 (2007/10/02)
Reaction of aldehydes R2-CHO with the new lithio derivatives of 2-benzothiazoles or pyridines R1-CH2-SO2-Het afforded the corresponding β-hydroxy sulfones which are stable in the pyridine series and generally unstable in the benzothiazole series except for anti derivatives 10a and 20c. t-Butyl-dimethyl silyl ethers of all the heterocyclic β-hydroxy sulfones have been obtained by oxidation of the corresponding anti and syn sulfides, which have been stereoselectively prepared from the epoxides 17, 19, 21 and 23.The lithium or tetrabutylammonium alkoxides of heterocyclic β-hydroxy sulfones undergo an intramolecular addition to the neighboring C=N group followed by an S to O benzothiazole (or pyridine) transfer, and simultaneous extrusion of sulfur dioxide, ejection of benzothiazol-2(3H)-one anion and formation of the corresponding olefins.From the data of twenty cases studied, it can be concluded that the final elimination is entirely antiperiplanar only for the alkoxides of β-hydroxy-BT- or Pyr-sulfones anti or syn bearing saturated aliphatic chains R1 and R2 and for anti derivatives with R1 = R2 = C6H5.Due to their equilibration however, the alkoxides of numerous derivatives of heterocyclic (3-methylbut-2-enyl) or (phenylmethyl) sulfones do not follow entirely the above antiperiplanar elimination. Keywords: heteroaromatic sulfones / intramolecular ipso reaction / organolithium derivatives / stereochemistry / eliminations / olefination
