107517-89-5Relevant academic research and scientific papers
Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes
Bandini, Marco,Battaglioli, Simone,Liu, Yang,Lombardi, Lorenzo,Menichetti, Arianna,Montalti, Marco,Valenti, Giovanni
, p. 4441 - 4446 (2021/06/28)
The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.
Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins
Wu, Xiaojin,Lu, Yunpeng,Hirao, Hajime,Zhou, Jianrong
, p. 6014 - 6020 (2013/06/26)
In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright
Mechanistic switch via subtle ligand modulation: Palladium-catalyzed synthesis of α,β-substituted styrenes via C-H bond functionalization
Flores-Gaspar, Areli,Martin, Ruben
, p. 1223 - 1228 (2011/06/26)
A new catalyst system able to efficiently perform the synthesis of styrenes via C-H bond functionalization and a subtle ligand modification are described. The high level of activity achieved allows for the synthesis of highly functionalized α,β-substituted styrenes, even the elusive E-configured trisubstituted olefins, in a regio- and stereoselective manner. Mechanistic experiments allowed for the identification of the corresponding synthetic intermediates.
Remaekable effect of subtle structural change of chiral pseudo-18-crown-6 on enantiomer-selectivity in complexation with chiral amino alcohols
Hirose, Keiji,Aksharanandana, Pakatip,Suzuki, Michiko,Wada, Kiyoshi,Naemura, Koichiro,Tobe, Yoshito
, p. 405 - 431 (2007/10/03)
Chiral receptors [(S,S)-1] and [(S,S,S,S)-2] having 1,2-dialkoxy-1-(3,5-dimethylphenyl)ethane and 1,2-dialkoxy-1-(3,5-dimethyl phenyl)cyclohexane as chiral building blocks, respectively, were prepared. Thermodynamic parameters of complexations of these and structurally related receptors [(S,S)-3] and [(S,S,S,S)-4] with 2-amino-l-propanol (5), 2-amino-2-phenylethanol (6), and 3-methylbutan-l-ol (7) in chloroform were determined. It was found that the host-guest systems that have same enantiomer-selectivity at 25°C showed opposite selectivity in the enthalpy term. For example, complexations of both (S,S)-1 and (S,S)-3 with 5 are R-selective at 25°C (ΔΔG = 2.2 and 3.8 kJ mol-1, respectively), whereas in terms of the enthalpy of complexation the former is S-selective (ΔΔH = 22 kJ mol-1) but the latter is R-selective (ΔΔH = 10 kJ mol-1).
