350586-99-1Relevant academic research and scientific papers
Stabilisation of 2,6-diarylpyridinium cation by through-space polar-π interactions
Padial, Joan Simo,Degelder, Rene,Fonsecaguerra, Celia,Bickelhaupt, F. Matthias,Mecinovic, Jasmin
supporting information, p. 6268 - 6271 (2014/06/09)
The through-space polar-π interactions between pyridinium ion and the adjacent aromatic rings in 2,6-diarylpyridines affect the pKavalues. Hammett analysis illustrates that the basicity of pyridines correlates well with the sigma values of the
Gallium tri-chloride derivatives of the sterically demanding pyridines 2,6-Ar2C6H3N (Ar = 2,4,6-Me3C6H2 or 2,4,6-Pri3C6H2)
Pell, Thomas,Mills, David P.,Blake, Alexander J.,Lewis, William,Liddle, Stephen T.
scheme or table, p. 120 - 125 (2010/04/04)
The sterically demanding pyridines 2,6-Ar2C6H3N [Ar = 2,4,6-Me3C6H2 (1) or 2,4,6-Pri3C6H2 (2)] were prepared by a palladium catalysed Kumada C-C coupling reaction in high yield. Pyridine 1 reacted with one equivalent of GaCl3 to afford the tetra-chloro gallate-pyridinium ion pair complex [GaCl4]-[2,6-(2,4,6-Me3C6H2)2C6H3NH]+ (3). Contrastingly, pyridine 2 reacted with one equivalent of GaCl3 to afford the anticipated donor-acceptor complex [GaCl3{2,6-(2,4,6-Pri3C6H2)2C6H3N}] (4). Complexes 1-4 have been characterised variously by single crystal X-ray diffraction, NMR, CHN, and mass spectrometry.
[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 11072 - 11081 (2010/11/16)
[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.
Highly active in situ catalysts for anti-Markovnikov hydration of terminal alkynes
Labonne, Aurelie,Kribber, Thomas,Hintermann, Lukas
, p. 5853 - 5856 (2007/10/03)
(Diagram presented) The anti-Markovnikov hydration of terminal alkynes to give aldehydes is catalyzed by complexes derived in situ from air-stable [CpRu(η6-naphthalene)]PF6 (C) and 6-aryl-2- diphenylphosphinopyridines (L). Ligands L are readily available from a modular synthesis. Increasing the size of the ligand C-6 aryl group in the order R = Ph mesityl 2,4,6-triisopropylphenyl (2,4,6-triphenyl)phenyl gave hydration catalysts of highest known activity.
