101043-55-4Relevant articles and documents
Greening the Valsartan Synthesis: Scale-up of Key Suzuki-Miyaura Coupling over Silia Cat DPP-Pd
Pandarus, Valerica,Desplantier-Giscard, Delphine,Gingras, Genevieve,Beland, Francois,Ciriminna, Rosaria,Pagliaro, Mario
, p. 1492 - 1497 (2013)
The study of the scale-up of the heterogeneous Suzuki-Miyaura coupling reaction in batch conditions between 2-chlorobenzonitrile and 4-tolylboronic acid, a key step in valsartan synthesis, to produce 4′-methyl-2- biphenylcarbonitrile over the SiliaCat DPP-Pd catalyst in ethanol under reflux allows to identify the optimal reaction conditions. The catalyst, regardless of limited Pd leaching, is not reusable, and the method can be effectively applied to the high yield synthesis of several coupling products, opening the route to efficient continuous coupling syntheses.
10-Hydroxy-10,9-boroxarophenanthrenes: Versatile synthetic intermediates to 3,4-benzocoumarins and triaryls
Zhou, Q. Jean,Worm, Karin,Dolle, Roland E.
, p. 5147 - 5149 (2004)
10-Hydroxy-10,9-boroxarophenanthrenes were obtained as unexpected major products upon BBr3-mediated O-demethylation of 2-methoxybiaryls. The formation likely proceeds via intramolecular electrophilic aromatic cyclization of a reactive dibromoaryloxyborane intermediate. Essentially quantitative yields of 10-hydroxy-10,9-boroxarophenanthrenes were also obtained from 2-hydroxybiaryl and BCl3/AlCl3 with use of a modified literature procedure. As synthetic intermediates, 10-hydroxy-10,9- boroxarophenanthrenes were efficiently converted to 3,4-benzocoumarins and triaryls through Pd-catalyzed CO insertion and Suzuki reaction.
Suzuki coupling with ligandless palladium and potassium fluoride
Kabalka,Namboodiri,Wang
, p. 775 - 775 (2001)
A ligandless palladium catalyzed Suzuki coupling reaction is described.
Palladium nanoparticles in ionic liquid by sputter deposition as catalysts for suzuki-miyaura coupling in water
Oda, Yoshiro,Hirano, Koji,Yoshii, Kazuki,Kuwabata, Susumu,Torimoto, Tsukasa,Miura, Masahiro
, p. 1069 - 1071 (2010)
Palladium nanoparticles in an ionic liquid prepared readily by sputter deposition efficiently catalyze the Suzuki-Miyaura coupling of hydrophobic as well as hydrophilic aryl halides in water.
Pd-catalyzed protecting-group-free cross-couplings of iodophenols with atom-economic triarylbismuth reagents
Rao, Maddali L.N.,Meka, Suresh
, (2020)
An efficient protocol for the protecting-group-free synthesis of unsymmetrical hydroxybiaryls via the Pd-catalyzed cross-couplings of unprotected iodophenols with triarylbismuth reagents is described. The presented protocols exhibits good to high yields of hydroxybiaryls.
Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols
Schmidt, Bernd,Riemer, Martin
, p. 1287 - 1297 (2017/03/27)
ortho-Aryl phenols, synthesized via protecting group free Suzuki–Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C–H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)2 without additional ligands.
A New Route to Phenols: Palladium-Catalyzed Cyclization and Oxidation of γ,δ-Unsaturated Ketones
Samadi, Sadaf,Orellana, Arturo
, p. 2472 - 2475 (2016/08/25)
We report a new strategy for the synthesis of phenols from acyclic unsaturated ketones in one pot. The reaction proceeds by palladium-catalyzed carbopalladation of an alkene with the enol form of the tethered ketone, generating a substituted cyclohexanone. Upon introduction of a terminal oxidant a palladium-catalyzed oxidation ensues to give the desired phenol. This approach allows the programming of phenol substituents on the acyclic substrate and therefore circumvents the limitations inherent in traditional syntheses of phenols.
