1048030-55-2Relevant academic research and scientific papers
Efficient synthesis of biologically interesting 3,4-diaryl-substituted succinimides and maleimides: Application of iron-catalyzed carbonylations
Prateeptongkum, Saisuree,Driller, Katrin Marie,Jackstell, Ralf,Spannenberg, Anke,Beller, Matthias
supporting information; experimental part, p. 9606 - 9615 (2010/10/18)
A straightforward two-step synthesis of trans-3,4-disubstituted succin imides through a palladium-catalyzed Sonogashira reaction and an iron-catalyzed double carbonylation is described. In situ oxidative dehydrogenation gave the corresponding 3,4-diarylmaleimides. By starting from readily available aryl and hetgeroaryl halides, a variety of new analogues and derivatives of bioactive 3,4-bisindolylmaleimides are obtained in good yield and selectivity.
Highly convenient, clean, fast, and reliable Sonogashira coupling reactions promoted by aminophosphine-based pincer complexes of palladium performed under additive-and amine-free reaction conditions
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 891 - 902 (2009/12/01)
Sequential addition of 1,1',1″-phosphine-triyltripiperidine and 1,3-diaminobenzene or resorci-nol to toluene solutions of (cyclooctadiene) palladium dichloride [Pd(cod)(Cl)2] under nitrogen in "one pot" almost quantitatively yielded the aminophos-phine-based pincer complexes {[C6H3-2,6-(XP{piperi-dinyl}2) 2]Pd(Cl)} (X = NH 1; X = O 2). Complex 1 (and to a minor extent 2) proved to be efficient Sonogashira catalysts, which allow the quantitative coupling of various electronically deactivated and/or sterically hindered and functionalized aryl iodides and aryl bromides with several alkynes as coupling partners within very short reaction times and low catalyst loadings. Importantly, in contrast to most of the Sonogashira catalysts, which either are both air-and moisture-sensitive and/or require the addition of co-catalysts, such as copper(I) iodide [Cul], for ex- ample, or a large excess of an amine, the coupling reactions were carried out without the use of amines, co-catalysts or other aditives and without exclusion of air and moisture. Moreover, the desired products were exclusively formed (no side-products were detected) without employing an excess of one of the substrates. Ethylene glycol and potassium phosphate (K3PO4) were found to be the ideal solvent and base for this transformation. Experimental observations strongly indicate that palladium nanoparticles are not the catalytically active form of 1 and 2. On the other hand, their transformation into another homogeneous catalytically active species cannot be excluded.
Iron-catalyzed sonogashira reactions
Carril, Monica,Correa, Arkaitz,Bolm, Carsten
supporting information; experimental part, p. 4862 - 4865 (2009/02/08)
(Chemical Equation Presented) With an iron will: Terminal alkynes undergo reaction with aryl and heteroaryl iodides in the presence of an iron catalyst formed from FeCl3 and N,N′-dimethylethylenediamine (dmeda, see scheme). The method displays
