6668-42-4Relevant academic research and scientific papers
Visible-Light Promoted Selective Imination of Unactivated C-H Bonds via Copper-nitrene Intermediates for the Synthesis of 2 H-Azirines
Feng, Liyan,Yang, Chao,Xia, Wujiong
, p. 8323 - 8327 (2019/10/16)
A novel strategy to trap iminyl radicals with copper ions has been developed at room temperature, the resulted high-valent Cu(III) imine intermediate resets quickly to form nitrene and then to furnish a 2H-azirine. This protocol with dual copper/photoredox catalyst enables the selective imination of unactivated C-H bonds under mild conditions with a broader scope. Moreover, this method also uncovers a novel ring-expansion rearrangement from cyclobutyl oxime derivatives to give the α-acylamino cyclopentanones.
Stereocontrol in Preparation of Cyclopalladated Alkylaromatic Oximes and Evaluation of Their Stereoselective Esterase-Type Catalytic Activity
Vatsadze, Sergey Z.,Medved'Ko, Aleksei V.,Kurzeev, Sergey A.,Pokrovskiy, Oleg I.,Parenago, Olga O.,Kostenko, Mikhail O.,Ananyev, Ivan V.,Lyssenko, Konstantin A.,Lemenovsky, Dmitri A.,Kazankov, Gregory M.,Lunin, Valery V.
, p. 3068 - 3075 (2017/09/05)
The stereochemistry of 2′-methylbutyrophenone oxime, the rates of ortho-palladation of its E- and Z-isomers, and catalytic activity of the respective Pd complexes were studied. The full stereoisomeric composition of oximes was established for the first time by means of supercritical fluid chromatography on chiral polysaccharide column. It was shown that enantiomeric excesses of both E/Z-isomers of (S)-2′-methylbutyrophenone oxime (1S) and (R)-2′-methylbutyrophenone oxime (1R) were equal to 92 ± 2. The cyclopalladation study revealed that while E-isomer is ortho-palladated very quickly its Z-counterpart does not enter this reaction. However, upon coordination to Pd(II), Z-oxime slowly isomerizes into E-form with fast subsequent cyclopalladation, so it was possible to perform ortho-palladation of E-oxime in kinetic resolution mode with removal of unreacted Z-oxime. Comparatively rare cis-structure of cyclopalladated oxime dimer was proved by means of single-crystal X-ray study. For the first time, it was shown that ortho-palladated chiral oximes behave as enantioselective catalyst in the hydrolysis of chiral esters.
Cycloplatination of aryl and ferrocenyl oximes by cis-[PtCl2(OSMe2)2] affording expected platinum(II) and unexpected platinum(IV) products
Ryabov, Alexander D.,Kazankov, Gregory M.,Panyashkina, Irina M.,Grozovsky, Oleg V.,Dyachenko, Oleg G.,Polyakov, Vladimir A.,Kuz'mina, Lyudmila G.
, p. 4385 - 4391 (2007/10/03)
Acetophenone, benzamide, ferrocenyl methyl ketone and ferrocenecarboxamide oximes reacted with cis-[PtCl2(dmso)2] (dmso = dimethyl sulfoxide) in refluxing methanol to afford the expected platina(II)cycles N,S-trans-[Pt(C-N)Cl(dmso)],
