63242-14-8Relevant articles and documents
Synthesis of Phosphanylferrocenecarboxamides Bearing Guanidinium Substituents and Their Application in the Palladium-Catalyzed Cross-Coupling of Boronic Acids with Acyl Chlorides
Charvátová, Hana,Císa?ová, Ivana,?těpni?ka, Petr
, p. 288 - 296 (2017/02/05)
Phosphanylferrocene donors bearing polar guanidinium substituents, namely acylguanidinium chloride, [Ph2PfcCONHC(NH2)NH2]Cl (1), and amidoguanidinium chloride, [Ph2PfcCONHCH2CH2NHC(NH2)NH2]Cl (2; fc = ferrocene-1,1′-diyl), have been prepared and characterized. As functional phosphane donors, they were employed in the synthesis of PdIIcomplexes bearing 2-[(dimethylamino)methyl-κN]phenyl-κC1(LNC) and η3-allyl supporting ligands, [(LNC)PdCl(L-κP)] and [(η3-C3H5)PdCl(L-κP)] (L = 1 and 2), respectively. These defined complexes as well as their surrogates generated in situ from the respective palladium(II) precursor and the phosphanylferrocene ligand were evaluated as catalysts for the coupling of boronic acids with acyl chlorides to give ketones in an aqueous biphasic system. The coupling reaction proceeded best with a simple catalyst formed from Pd(OAc)2and ligand 2, which (at 0.2 mol-% Pd loading) produced substituted benzophenones from benzoyl chlorides and benzeneboronic acids in very good yields. These yields could then be further improved by a proper choice of the reaction partners. Analogous reactions involving aliphatic substrates generally afforded lower yields.
Synthesis, structural characterization, and catalytic evaluation of phosphinoferrocene ligands bearing extended urea-amide substituents
Solarova, Hana,Cisarova, Ivana,Stepnicka, Petr
, p. 4131 - 4147 (2014/10/15)
New phosphinoferrocene ligands bearing extended polar amidourea pendants with the general formula Ph2PfcCONHCH2CH 2NHCONR2 (1; R2 = H2 (b), H/Et (c), Me2 (d), H/Ph (e)) and their model bis-amide Ph 2PfcCONHCH2CH2NHCOCH3 (1a) were prepared in good yields by amidation of 1′-(diphenylphosphino)ferrocene-1- carboxylic acid (Hdpf) with the appropriate amines in the presence of peptide coupling reagents. These ferrocene-based phosphinoureas were further employed as ligands in palladium(II) complexes with η3-allyl and NC-chelating supporting ligands: viz., [PdCl(η3-C 3H5)(1-κP)] (5a-e) and [PdCl(LNC)(1- κP)] (6a-e; LNC = [2-(dimethylamino-κN)methyl]phenyl- κC1). Both the free ligands and their Pd(II) complexes were characterized by spectroscopic methods (multinuclear NMR, IR, and MS) and by elemental analysis. The molecular structures of 1b·CH3OH, 1c, 5b,c, 6a, and two additional model complexes, [PdCl(η3-C 3H5)(Hdpf-κP)] (5f) and [PdCl(η3- C3H5)(Ph2PfcCONH2-κP)] (5g), were determined by single-crystal X-ray diffraction analysis. All Pd(II) complexes were evaluated as catalysts in the cross-coupling of boronic acids and acyl halides to give ketones in a toluene/water biphasic mixture. Extensive reaction studies with compound 5e, which not only exerts good catalytic activity but is also readily accessible in a defined crystalline form, demonstrated efficient coupling reactivity for unsaturated substrates such as (substituted) benzeneboronic acids and benzoyl chlorides. The results also revealed that reaction difficulties encountered with less reactive substrates (e.g., insoluble aromatic boronic acids and all saturated aliphatic boronic acids) can be avoided by properly selecting the reaction partners, for example through transposition of substituents between reaction partners. Three representative benzophenones (4-fluoro-, 4-nitro-, and 4,4′-dinitrobenzophenone) were structurally characterized by single-crystal X-ray crystallography.
Synthesis and biological activities of N,N-dimethyl-2-propen-1-amine derivatives
Conti, R. De,Gimenez, S. M. N.,Haun, M.,Pilli, R. A.,Castro, S. L. De,Duran, N.
, p. 915 - 918 (2007/10/03)
The synthesis of several 3-(4'-bromo-4-yl)-3-(4-X-phenyl)-N,N-dimethyl-2-propen-1-amine derivatives is described.These compounds are potential trypanocide agents with relative low acute toxicities. the inhibition of growth of Escherichia coli by these drugs with different para-substitution on the phenyl moiety and their trypanocidal activities against epimastigote from Trypanosoma cruzi were investigated. - Keywords: Chagas's disease; trypanocide; Trypanosoma cruzi; aminopropene.
