138487-20-4Relevant articles and documents
Sonogashira coupling of aryl halides catalyzed by palladium on charcoal
Novak, Zoltan,Szabo, Andras,Repasi, Jozsef,Kotschy, Andras
, p. 3327 - 3329 (2003)
With the proper choice of solvent, palladium on charcoal acts as an efficient catalyst in the Sonogashira cross-coupling reaction of aryl bromides. The catalytically active species in the process is probably palladium, which leaches into the solution but
Modification of the 4-phenylbutyl side chain of potent 3-benzazepine-based GluN2B receptor antagonists
Wagner, Marina,Schepmann, Dirk,Ametamey, Simon M.,Wünsch, Bernhard
supporting information, p. 3559 - 3567 (2019/07/03)
Excitotoxicity driven by overactivation of NMDA receptors represents a major mechanism of acute and chronic neurological and neurodegenerative disorders. Negative allosteric modulators interacting with the ifenprodil binding site of the NMDA receptor are able to interrupt this ongoing neurodamaging process. Starting from the potent 3-benzazepine-1,7-diol 4a novel NMDA receptor antagonists were designed by modification of the N-(4-phenylbutyl) side chain. With respect to developing novel fluorinated PET tracers, regioisomeric fluoroethoxy derivatives 11, 12, 14, and 15 were synthesized. Analogs 19 and 20 with various heteroaryl moieties at the end of the N-side chain were prepared by Sonogashira reaction and nucleophilic substitution. The fluoroethyl triazole 37 was obtained by 1,3-dipolar cycloaddition. In several new ligands, the flexibility of the (hetero)arylbutyl side chain was restricted by incorporation of a triple bond. The affinity towards the ifenprodil binding site was tested in an established competition assay using [3H]ifenprodil as radioligand. Introduction of a fluoroethoxy moiety at the terminal phenyl ring, replacement of the terminal phenyl ring by a heteroaryl ring and incorporation of a triple bond into the butyl spacer led to considerable reduction of GluN2B affinity. The phenol 15 (Ki = 193 nM) bearing a p-fluoroethoxy moiety at the terminal phenyl ring represents the most promising GluN2B ligand of this series of compounds. With exception of 15 showing moderate σ2 affinity (Ki = 79 nM), the interaction of synthesized 3-benzazepines towards the PCP binding site of the NMDA receptor, σ1 and σ2 receptors was rather low (Ki > 100 nM).
A versatile and efficient palladium-meta-terarylphosphine catalyst for the copper-free sonogashira coupling of (hetero-)aryl chlorides and alkynes
Yang, Yong,Chew, Xinying,Johannes, Charles W.,Robins, Edward G.,Jong, Howard,Lim, Yee Hwee
, p. 7184 - 7192 (2015/01/16)
A novel meta-terarylphosphine ligand, CyPhine, was developed and found to be a highly active promoter of copper-free Sonogashira cross-coupling reactions when combined in situ with a palladium source. The evolutionary m-terarylphosphine ligand architectur
Ligand-free sonogashira coupling reactions with heterogeneous Pd/C as the catalyst
Mori, Shigeki,Yanase, Takayoshi,Aoyagi, Satoka,Monguchi, Yasunari,Maegawa, Tomohiro,Sajiki, Hironao
supporting information; experimental part, p. 6994 - 6999 (2009/07/18)
A variety of aryl iodides were coupled with aromatic and aliphatic terminal alkynes to give the corresponding 1,2-disubstituted aromatic alkynes in good yields by using only 0.4 mol % of the heterogeneous 10% Pd/C as the catalyst without a ligand, copper
