168063-43-2Relevant academic research and scientific papers
The cyclopalladation reaction of benzylamine revisited
Albert, Joan,Granell, Jaume,Tavera, Raquel
, p. 287 - 291 (2003)
The reaction of benzylamine and palladium(II) acetate in a one-to-one molar ratio in toluene or in glacial acetic acid at 60 °C for 24 h produced the acetato bridged cyclopalladated dimer of benzylamine (μ-OAc)2[Pd(C6H4 CH2NH2)]2 (1) in yields of 40-75% and of 20-40%, respectively. In addition, mixtures of compounds 1, 1d1 of formula [(3-DC6H3CH2NH2)Pd](μ- OAc)2[Pd(C6H4CH2NH2)] and 1d2 of formula (μ-OAc)2[Pd(3-DC6H3 CH2NH2)]2 were obtained when benzylamine and palladium(II) acetate in a one-to-one molar were treated in monodeuterated acetic acid (DOAc) at 60 °C for 24 h. These mixtures were isolated in yields of 10-30% and deuterium contents in the range between 0.7 and 0.9. Furthermore, the treatment of benzylamine and palladium(II) acetate in a one-to-one molar ratio under reflux of glacial acetic acid for 45 min produced the acetato bridged endo-cyclopalladated dimer of benzyl-benzylidene-amine (μ-OAc)2[Pd(C6H4 CH=NCH2C6H5)] (compound 4), which was isolated in 14% yield relative to the initial palladium(II) acetate, together with other unidentified compounds. 2002 Elsevier Science Ltd. All rights reserved.
Solvent-free cyclopalladation on silica gel
Smoliakova, Irina P.,Wood, Jessica L.,Stepanova, Valeria A.,Mawo, Relindis Y.
, p. 360 - 364 (2010/05/01)
Tertiary, secondary and primary benzylamines, as well as structurally different oxazolines readily reacted with Pd(OAc)2 on silica gel to form cyclopalladated complexes containing a five or six-membered palladacycle with a (sp2)C-Pd or (sp3)C-Pd bond. The complexes were obtained in 45-98% yield, which is comparable with or exceeds the yields reported for preparation of the same compounds in solution. Aliphatic (sp3)C-H bond activation took place in the cyclopalladation of (S)-2-tert-butyl-4-phenyl-2-oxazoline on SiO2 leading to the exclusive formation of the corresponding endo palladacycle, whereas two products were reported for the same reaction performed in AcOH.
