1333412-75-1Relevant academic research and scientific papers
Indium-assisted aluminium-based stereoselective allylation of prostereogenic α,α-disubstituted cycloalkanones and imines
Reddy, Chennakesava,Babu, Srinivasarao Arulananda,Aslam, Nayyar Ahmad
, p. 40199 - 40213 (2014/12/10)
The use of a catalytic amount of InCl3in combination with Al0for the allylation of a variety of prostereogenic α,α-disubstituted (hindered) cycloalkanones, 1,2-dione-based systems and various imino systems (CN functional groups) is reported. The stereoselective InCl3-catalyzed Al-based allylation of various 2-substituted-2-carbethoxycycloalkanones gave the corresponding products with moderate to excellent diastereoselectivity. The allylation and propargylation of imines including α-imino esters using a catalytic amount of InCl3in combination with Al0gave the corresponding allylated and propargylated compounds in moderate to good yields. If γ-substituted allylic halides were added to imino compounds, low to very good diastereoselectivity was obtained. The allylation of chiral N-tert-butylsulfinyl imine systems gave the corresponding products in moderate yields with good to excellent diastereoselectivity. This journal is
Synthesis, structure and catalytic properties of CNN pincer palladium(II) and ruthenium(II) complexes with N-substituted-2-aminomethyl-6-phenylpyridines
Wang, Tao,Hao, Xin-Qi,Zhang, Xiao-Xue,Gong, Jun-Fang,Song, Mao-Ping
experimental part, p. 8964 - 8976 (2011/10/31)
N-substituted-2-aminomethyl-6-phenylpyridines 2a-c have been easily prepared from commercially available 6-bromo-2-picolinaldehyde in two steps. Reaction of 2a-c with PdCl2 in toluene in the presence of triethylamine gave the CNN pincer Pd(ii) complexes 3a-c in 18-28% yields. The CNN pincer Ru(ii) complex 5 containing a Ru-NHR functionality could be obtained in a 71% yield by treatment of 2c with a Ru(ii) precursor instead of PdCl 2. Additionally, the related CNN pincer Ru(ii) complex 7 containing a Ru-NH2 functionality has been synthesized by the reaction of 2-aminomethyl-6-phenylpyridine with the same Ru(ii) precursor in a 68% yield. All the new compounds were characterized by elemental analysis (MS for ligands), 1H, 13C NMR, 31P{1H} NMR (for Ru complexes) and IR spectra. Molecular structures of Pd complex 3c as well as Ru complexes 5 and 7 have been determined by X-ray single-crystal diffraction. The obtained Pd complexes 3a-c were effective catalysts for the allylation of aldehydes as well as for three-component allylation of aldehydes, arylamines and allyltributyltin and their activity was found to be much higher than a related NCN Pd(ii) pincer in the allylation of aldehyde. On the other hand, the two new CNN pincer Ru(ii) complexes 5 and 7 displayed excellent catalytic activity in the transfer hydrogenation of ketones in refluxing 2-propanol with the latter being much more active. The final TOF values were up to 4510 h-1 with 0.01 mol% of 5 and 220800 h-1 with 0.005 mol% of 7, respectively. The Royal Society of Chemistry 2011.
