362622-68-2Relevant academic research and scientific papers
Cobalt-catalyzed carbonylative synthesis of phthalimides from n-(pyridin-2-ylmethyl)benzamides with tfben as the co source
Fu, Lu-Yang,Wu, Xiao-Feng,Ying, Jun
, (2019/10/08)
A cobalt-catalyzed direct carbonylative synthesis of phthalimide motifs from N-(pyridin-2-ylmethyl)benzamides has been developed. Various phthalimide derivatives were obtained in moderate to excellent yields (up to 98percent) by using 2-picolylamine as an efficient directing group and benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate.
Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: Regioselective oxidative cycloaddition of aromatic amides to alkynes
Shiota, Hirotaka,Ano, Yusuke,Aihara, Yoshinori,Fukumoto, Yoshiya,Chatani, Naoto
experimental part, p. 14952 - 14955 (2011/11/05)
Although the pioneering example of ortho metalation involving cleavage of C-H bonds was achieved using a nickel complex (Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544), no examples of catalysis using nickel complexes have been reported. In this work, the Ni-catalyzed transformation of ortho C-H bonds utilizing chelation assistance, such as oxidative cycloaddition of aromatic amides with alkynes, has been achieved.
Derivatization of 4-(dimethylamino)benzamide to dual fluorescent ionophores: Divergent spectroscopic effects dependent on N or O amide chelation
Malval, Jean-Pierre,Lapouyade, Rene
, p. 2439 - 2451 (2007/10/03)
Starting from the pentafluorophenyl ester of 4-(dimethylamino)benzoic acid, two dual fluorescent amide ligands with aza-15-crown-5 and 2-(aminomethyl)pyridine were obtained for sensing, respectively, alkali (alkaline-earth) and transition (heavy) metal cations. The crystal structure of the copper(II) complex is reported. The Cu2+ is coordinated through the pyridine N- and amide O-atoms of two symmetry-related ligands. The azacrown-directed Ca-chelation to the N-atom of the amide leads to a slight quenching of the two fluorescence bands. In contrast, the pyridine directed Cu11-chelation to the O-atom of the amide enhances the short-wavelength emission 17-fold over the locally excited state (LE), quenching the twisted intramolecular charge-transfer (TICT) emission, and, as a result, the intensity ratio I(LE)/I(TICT) provides an accurate and sensitive measurement of the Cu11 concentration. These different cation effects are dependent on which atom (N vs. O) of the amide function participates in cation coordination: while the Ca2+ interaction with the N-atom electron pair leads to the deconjugation of the amide N-atom from the fluorophore, Cu2+ interaction with the lone pair of the O-atom of the carbonyl group increases the energy of the n-π* but also of the 1La transition and therefore close the channel to the TICT state.
