92115-23-6Relevant academic research and scientific papers
Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates
Chen, Yi-Hung,Gra?l, Simon,Knochel, Paul
, p. 1108 - 1111 (2018/01/01)
Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25 °C within 2–4 h in the presence of 2.5–5.0 % CoCl2?2 LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56 % overall yield by using this cobalt-catalyzed amination as the key step.
Palladium-catalyzed amination of aryl bromides utilizing arene-chromium complexes as ligands
Kamikawa, Ken,Sugimoto, Suguru,Uemura, Motokazu
, p. 8407 - 8410 (2007/10/03)
The arene - chromium complexes of o-diphenylphosphino α- phenylethylamine or α-phenylethyl methyl ether derivatives were examined with regard to their activity as ligands for palladium(0)-catalyzed aryl amination of aryl bromides with a variety of amines. Both steric and electronic factors were found to be significant for the efficient palladium- catalyzed aryl amination reactions. Modulation of the inductive capacity of the arylphosphine atom was achieved by photoinduced ligand exchange of one carbonyl of the chromium tripode in the presence of electron-donating triphenylphosphine or phosphite. Among these arene - chromium ligands, the use of the monophosphineor monophosphite-(dicarbonyl)chromium of N,N- dimethyl α-(o-diphenylphosphino)phenylethylamine and methyl α-(o- diphenylphosphino)phenylethyl ether produced the palladium(0)-catalyzed aryl amination products with cyclic amines or acyclic secondary amines in high yields; the corresponding strong electron-withdrawing tricarbonylchromium complex resulted in a modest yield of the aryl amination.
Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. The Formation of Alkyldiarylamines and Triarylamines
Haga, Kazuo,Oohashi, Masayuki,Kaneko, Ryohei
, p. 1586 - 1590 (2007/10/02)
Condensation of 1,4-cyclohexanedione with N-alkylarylamines gives N-alkyl-N-arylanilines, and that with diarylamines gives triarylamines.A mechanism involving dehydration of monoenamines of the 1,4-dione is proposed for the reaction.Relative rates of substituted N-ethylanilines on competitive reactions plotted vs.Hammet's ? values gave -2.0 as the ρ value.In separate reactions, however, a different tendency is noted for the yield, that is, the ease of reactions with p-chloro and p-nitro derivatives.This discrepancy is explained in terms of acidities of the conjugate acids of the amines used as the actual catalysts.
