1436849-27-2Relevant academic research and scientific papers
Nickel(II)-catalyzed direct arylation of C-H bonds in aromatic amides containing an 8-aminoquinoline moiety as a directing group
Yokota, Ayana,Aihara, Yoshinori,Chatani, Naoto
, p. 11922 - 11932 (2014)
Arylation via the cleavage of the ortho C-H bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety with aryl iodides is reported. The reaction shows a high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered C-H bonds in the reaction of meta-substituted aromatic amides, irrespective of the electronic nature of the substituents. Electron-withdrawing groups on the aromatic amides facilitate the reaction. Various mechanistic experiments, such as deuterium labeling experiments, Hammett studies, competition experiments, and radical trap experiments, have been made for better understanding the reaction mechanism. It is found that the cleavage of C-H bonds is reversible on the basis of the deuterium labeling experiments. Both Ni(II) and Ni(0) show a high catalytic activity, but the results of mechanistic experiments suggest that a Ni(0)/Ni(II) catalytic cycle is not involved. (Chemical Equation Presented).
Aryne Multicomponent Reactions by Directed C?H Activation
Sunnam, Sunil Kumar,Belani, Jitendra D.
, p. 8846 - 8850 (2021/05/31)
Arylation via ortho C?H activation by the aid of directing groups has been explored recently by many researchers. Herein, a palladium-catalyzed C?H arylation using 8-aminoquinoline as a bidentate directing group has been developed. The reaction furnishes only C?H arylation, unlike previous methods where cyclization to corresponding isoquinolones is observed. More interestingly, sequential C?H functionalization was observed when methylacrylate and acrylonitrile was added; this led to C?H olefination with the aryl group, which was installed from the aryne precursor.
Ruthenium-catalyzed direct arylation of C-H bonds in aromatic amides containing a bidentate directing group: Significant electronic effects on arylation
Aihara, Yoshinori,Chatani, Naoto
, p. 664 - 670 (2013/03/29)
Arylation of ortho C-H bonds is achieved by a ruthenium-catalyzed reaction of aromatic amides having an 8-aminoquinoline moiety with aryl bromides. The reaction shows high functional group compatibility. The reaction proceeds in a highly selective manner at the less hindered C-H bonds of meta-substituted aromatic amides. Significant electronic effects are observed in Hammett plots. Electron-withdrawing groups on the aromatic amides facilitate the reaction. In contrast, both electron-donating groups and electron-withdrawing groups on aryl bromides accelerate the reaction. The Royal Society of Chemistry 2013.
