205529-19-7Relevant academic research and scientific papers
Application of palladium complexes bearing acyclic amino(hydrazido)carbene ligands as catalysts for copper-free Sonogashira cross-coupling
Timofeeva, Svetlana A.,Kinzhalov, Mikhail A.,Valishina, Elena A.,Luzyanin, Konstantin V.,Boyarskiy, Vadim P.,Buslaeva, Tatyana M.,Haukka, Matti,Kukushkin, Vadim Yu.
, p. 449 - 456 (2015)
Abstract Metal-mediated coupling of one isocyanide in cis-[PdCl2(CNR1)2] (R1 = C6H11 (Cy) 1, tBu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3
The copper-free Sonogashira cross-coupling reaction promoted by palladium complexes of nitrogen-containing chelating ligands in neat water at room temperature
Zhong, Hong,Wang, Jinyun,Li, Liuyi,Wang, Ruihu
, p. 2098 - 2103 (2014/01/17)
The commercially available 2,2′-dipyridylamine was used as a supporting ligand in the palladium-catalyzed Sonogashira cross-coupling reaction. The reactions between aryl iodides and terminal alkynes with different steric hindrance can be efficiently performed in the absence of copper in neat water at room temperature. The superior catalytic performance of the catalytic system was attributed to water solubility of the palladium 2,2′- dipyridylamine complex. Palladium nanoparticles with small size and narrow size distribution were formed after the cross-coupling reaction.
Ligand-free copper oxide nanoparticle-catalyzed sonogashira coupling reaction
Yuan, Yu,Zhu, Haitao,Zhao, Dongbo,Zhang, Li
experimental part, p. 1792 - 1798 (2011/07/08)
The catalytic Sonogashira coupling reaction of terminal alkynes and aryl halides is developed using copper(II) oxide nanoparticles as catalyst in dimethyl sulfoxide. The procedure is experimentally simple, general, efficient, and free from addition of ext
Stereoselective addition of diphenylphosphine to substituted diphenylethynes: Synthetic, NMR and X-ray crystallographic studies
Bookham, Jonathan L.,Smithies, Darren M.,Wright, Anna,Thornton-Pett, Mark,McFarlane, William
, p. 811 - 818 (2007/10/03)
The base-catalysed addition of diphenylphosphine to the substituted diphenylethynes RC≡CR′ (R = Ph, R′ = Ph, o-tolyl, m-tolyl or 2-biphenyl; R = m-tolyl, R′ = o-tolyl or m-tolyl) yielded Ph2PC(R)=CHR′ and/or Ph2PCH(R)CH(R′)PPh2. Proton, 13C, 13P and two-dimensional rotating frame Overhauser enhancement 1H NMR spectra have been used to determine the stereochemical pathways of the reactions and the stereochemistry of the products. In general the more hindered alkynes undergo monoaddition ultimately to yield phosphinoalkenes with the Ph2P attached to the carbon bearing the least bulky substituent and cis to the olefinic proton, while for the less hindered alkynes the trans isomer is formed initially and this then reacts further to give mesolerythro-diphosphinoalkanes. Bis(o-tolyl)ethyne does not react with Ph2PH under the same conditions. Crystal structures were determined for E- and Z-Ph2P(Ph)C=CHPh and show distortions of interbond angles consistent with the pattern of strain implied by the foregoing reactions. The sulfides of the phosphinoalkenes and the Mo(CO)4 complexes of the diphosphinoalkanes were also prepared and their 1H, 13C and 31P NMR spectra recorded. In several cases the pattern of 13CO NMR signals for the complexes was used unambiguously to determine the stereochemistry of the parent diphosphines.
