110615-04-8Relevant academic research and scientific papers
Maleimide-assisted anti-Markovnikov Wacker-type oxidation of vinylarenes using molecular oxygen as a terminal oxidant
Nakaoka, Sonoe,Murakami, Yuka,Kataoka, Yasutaka,Ura, Yasuyuki
, p. 335 - 338 (2016)
Arylacetaldehydes were successfully synthesized by the anti-Markovnikov Wacker-type oxidation of vinylarenes using 1 atm O2 as a terminal oxidant under mild conditions. Electron-deficient alkenes, such as maleic anhydride and maleimides, were effective additives and would operate as ligands to stabilize the Pd(0) species during the reaction.
Stereoselective Synthesis of Vinylboronates by Rh-Catalyzed Borylation of Stereoisomeric Mixtures
Li, Shenhuan,Li, Jie,Xia, Tianlai,Zhao, Wanxiang
supporting information, p. 462 - 468 (2019/03/28)
The stereoselective preparation of vinylboronates via rhodium-catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh-catalyzed borylation-isomerization sequence. The isomerization of (Z)-vinylboronates to (E)-isomers was also demonstrated.
Oxidation of styrene and of some derivatives with H2O 2 catalyzed by novel imidazolium-containing manganese porphyrins: A mechanistic and thermodynamic interpretation
De Paula, Rodrigo,Sim?es, Mário M.Q.,Neves, M. Graa P.M.S.,Cavaleiro, José A.S.
experimental part, p. 1 - 11 (2011/10/05)
The oxidation of styrene and derivatives with H2O2 catalyzed by manganese porphyrins in acetonitrile is described. The effect of the imidazolium substituent on the catalytic efficiency has been also considered. The thermodynamic analysis has indicated that enthalpy rules styrene oxidation when catalysts Mn(Porph)-1 and Mn(Porph)-2 are used whereas the entropy is the driven force for Mn(Porph)-3 and Mn(Porph)-4 catalyzed reactions. Interestingly, an enthalpy-entropy compensation phenomenon is observed when comparing the thermodynamic results obtained for catalysts Mn(Porph)-3 and Mn(Porph)-4. Hammett plots for the studied manganese porphyrins provided small ρ-values, and this is typical for multi-step reactions, indicating that there is no significant charge separation in the transition state. For Mn(Porph)-1 and Mn(Porph)-2 the formation of multiple active species can be put forward whereas for Mn(Porph)-3 and Mn(Porph)-4 a concerted-type mechanism, via metalloxetane intermediate, fits well with the values obtained for those catalysts. The imidazolium-based catalysts have shown to be efficient catalysts in styrene and derivatives oxidation with hydrogen peroxide.
