31416-74-7Relevant articles and documents
Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E, E)-1,3-Dienes
Dethe, Dattatraya H.,Beeralingappa, Nagabhushana C.,Uike, Amar
, p. 3444 - 3455 (2021/02/16)
An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst.
Synthesis of (E)-cinnamyl ester derivatives via a greener Steglich esterification
Lutjen, Andrew B.,Quirk, Mackenzie A.,Barbera, Allycia M.,Kolonko, Erin M.
, p. 5291 - 5298 (2018/05/04)
Cinnamic acid derivatives are known antifungal, antimicrobial, antioxidant, and anticancer compounds. We have developed a facile and mild methodology for the synthesis of (E)-cinnamate derivatives using a modified Steglich esterification of (E)-cinnamic acid. Using acetonitrile as the solvent, rather than the typical chlorinated solvent, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) as the coupling agent enables ester conversion in 45 min with mild heating (40–45 °C) and an average yield of 70% without need for further purification. These conditions were used to couple (E)-cinnamic acid with 1° and 2° aliphatic alcohols, benzylic and allylic alcohols, and phenols. This work demonstrates a facile and greener methodology for Steglich esterification reactions.
A highly efficient Pd/CuI-catalyzed oxidative alkoxycarbonylation of α-olefins to unsaturated esters
Maffei, Mathias,Giacoia, Gabriele,Mancuso, Raffaella,Gabriele, Bartolo,Motti, Elena,Costa, Mirco,Della Ca’, Nicola
, p. 435 - 443 (2016/12/16)
A new protocol for the alkoxycarbonylation of α-olefins to the corresponding unsaturated esters has been developed. Differently substituted styrenes were selectively converted to cinnamate derivatives, via C[sbnd]H bond functionalization. Various palladium sources, including heterogeneous ones, in combination with CuI exhibited a high catalytic efficiency using oxygen as the most cheap oxidant. Monocarbonylated products were obtained in good yields and high chemoselectivity working with a low CO pressure (2 atm) and an excess of air (35 atm) avoiding in this way explosion risks. Commercial cinnamate derivatives were prepared in good to excellent yields by this very simple one-pot procedure.