63873-32-5Relevant academic research and scientific papers
Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts
Alsters, Paul L.,Chou, Khi Chhay,De Wildeman, Stefaan M. A.,Faber, Teresa,Hadavi, Darya,Han, Peiliang,Quaedflieg, Peter J. L. M.,Schwalb Freire, Alfonso J.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.
supporting information, p. 10102 - 10112 (2021/08/03)
The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.
Use of (cyclopentadienone)iron tricarbonyl complexes for c-n bond formation reactions between amines and alcohols
Brown, Thomas J.,Cumbes, Madeleine,Diorazio, Louis J.,Clarkson, Guy J.,Wills, Martin
, p. 10489 - 10503 (2018/05/31)
The application of a series of (cyclopentadienone)iron tricarbonyl complexes to "borrowing hydrogen" reactions between amines and alcohols was completed in order to assess their catalytic activity. The electronic variation of the aromatic groups flanking the C?O of the cyclopentadienone influenced the efficiency of the reactions; however, in other cases, the Kn?lker catalyst 1, containing trimethylsilyl groups flanking the cyclopentadienone ketone, gave the best results. In some cases, the change of the ratio of amine to alcohol improves the conversion significantly. The application of iron catalysts to the synthesis of a range of amines, including unsaturated amines, was investigated.
Earth-abundant photocatalytic systems for the visible-light-driven reduction of CO2 to CO
Rosas-Hernández, Alonso,Steinlechner, Christoph,Junge, Henrik,Beller, Matthias
supporting information, p. 2356 - 2360 (2017/07/24)
Herein, we report a highly selective photocatalytic system, based on an in situ copper photosensitizer and an iron catalyst, for the reduction of CO2 to CO. Turnover numbers (TON) up to 487 (5 h) with selectivities up to 99% and ΦCO = 13.3% were observed. Stern-Volmer analysis allowed us to establish a reductive quenching mechanism between the Cu PS and electron donor.
Transfer hydrogenation of ethyl levulinate to γ-valerolactone catalyzed by iron complexes
Dai, Nan,Shang, Rui,Fu, Mingchen,Fu, Yao
supporting information, p. 405 - 408 (2015/04/22)
Conversion of biomass-derived ethyl levulinate to γ-valerolactone is realized by using homogeneous iron-catalyzed transfer hydrogenation (CTH). By utilizing Casey's catalyst and cheap isopropanol as hydrogen source, γ-valerolactone can be generated in 95% yield. Addition of catalytic amount of base is important to achieve good yield.
Total synthesis of an exceptional brominated 4-pyrone derivative of algal origin: An exercise in gold catalysis and alkyne
Hoffmeister, Laura,Fukuda, Tsutomu,Pototschnig, Gerit,Frstner, Alois
supporting information, p. 4529 - 4533 (2015/03/14)
A concise approach to the algal metabolite 1 is described, which also determines the previously unknown stereostructure of this natural product. Compound 1 is distinguished by a rare brominated 4-pyrone nucleus linked as a ketene-acetal to a polyunsaturated macrocyclic scaffold comprising an extra homoallylic bromide entity. The synthesis of 1 is based on the elaboration and selective functionalization of the linear precursor 23 endowed with no less than six different sites of unsaturation including the highly enolized oxo-alkanoate function. Key to success was the formation of the 2-alkoxy-4-pyrone ring by a novel gold-catalyzed transformation which engages only the acetylenic β-ketoester substructure of 23 but leaves all otherπ-bonds untouched. The synthesis was completed by a ring-closing alkyne metathesis to forge the signature cycloalkyne motif of 1 followed by selective bromination of the ketene-acetal site in the resulting product 27 without touching the skipped diene-yne substructure resident within the macrocyclic tether.
Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: Synthesis, computational studies and application in reductive amination
Moulin, Solenne,Dentel, Helene,Pagnoux-Ozherelyeva, Anastassiya,Gaillard, Sylvain,Poater, Albert,Cavallo, Luigi,Lohier, Jean-Francois,Renaud, Jean-Luc
supporting information, p. 17881 - 17890 (2014/01/17)
Reductive amination under hydrogen pressure is a valuable process in organic chemistry to access amine derivatives from aldehydes or ketones. Knoelker's complex has been shown to be an efficient iron catalyst in this reaction. To determine the influence of the substituents on the cyclopentadienone ancillary ligand, a series of modified Knoelker's complexes was synthesised and fully characterised. These complexes were also transformed into their analogous acetonitrile iron-dicarbonyl complexes. Catalytic activities of these complexes were evaluated and compared in a model reaction. The scope of this reaction is also reported. For mechanistic insights, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Festival of amination: Two series of modified Knoelker's complexes were synthesised and applied in the reductive amination of various carbonyl derivatives with primary or secondary amines (see scheme, TIPS = triisopropylsilyl). For a mechanistic insight, deuterium-labelling experiments and DFT calculations were undertaken and are also presented. Copyright
Air-stable, nitrile-ligated (cyclopentadienone)iron dicarbonyl compounds as transfer reduction and oxidation catalysts
Plank, Taylor N.,Drake, Jessica L.,Kim, Daniel K.,Funk, Timothy W.
supporting information; experimental part, p. 597 - 601 (2012/05/04)
A series of air-stable, nitrile-ligated (cyclopentadienone)iron dicarbonyl compounds was synthesized and their activities as catalysts in the transfer reduction of acetophenone were explored. While all were active catalysts, the acetonitrile adduct was chosen for further study and was found to be active in the transfer reduction of aldehydes and ketones and in the Oppenauer-type oxidation of secondary alcohols. The acetonitrile catalyst exhibited activities similar to those of an analogous air-sensitive iron hydride, but unlike the iron hydride it was unreactive in carbonyl reductions using hydrogen gas. Copyright
Nickel-catalyzed cross-coupling of primary alkyl halides with phenylethynyl- and trimethylsilyethynyllithium reagents
Xu, Guoqiang,Li, Xiaoyan,Sun, Hongjian
supporting information; experimental part, p. 3011 - 3014 (2011/08/22)
A highly efficient alkyl-alkynyl coupling system is described which is promoted by a well-defined and moisture-stable pincer complex [NiCl{C 6H3-2,6-(OPPh2)2}] (1). Non-activated alkyl halides could be efficient
Ytterbium(II)-aromatic imine dianion complexes-catalyzed isomerization of terminal alkynes
Makioka, Yoshikazu,Saiki, Akira,Takaki, Ken,Taniguchi, Yuki,Kitamura, Tsugio,Fujiwara, Yuzo
, p. 27 - 28 (2007/10/03)
Ytterbium-aromatic imine dianion complexes, easily prepared from ytterbium metal and aromatic imines, can act as effective catalysts for the isomerization of terminal alkynes to afford internal alkynes in good to high yields.
Isomerization of terminal alkynes catalyzed by itterbium(II)-aromatic imine complexes
Makioka, Yoshikazu,Taniguchi, Yuki,Kitamura, Tsugio,Fujiwara, Yuzo,Saiki, Akira,Takaki, Ken
, p. 349 - 356 (2007/10/03)
Ytterbium-aromatic imine dianion complexes 2, which can easily be prepared from metallic ytterbium and aromatic imines 1, can act as effective catalysts for the isomerization of terminal alkynes 3 under mild conditions to afford internal alk-2-ynes 4 in good yields.In the reaction of 1-hexene 3a, 2-hexyne 3a, 2-hexyne 4a can be simply obtained by trap-to-trap distillation and the catalytic system can be reused for the isomerization of 3a without other treatments. - Keywords: lanthanoid-imine complex; terminal alkyne; isomerization; alk-2-yne
