The combination of lanthanum(iii) triflate, sulfur, and dimethyl sulfoxide prompted a facile, direct preparation of 2,5-diformylfuran from glucose and fructose. The one-step dehydration/oxidation of fructose afforded 2,5-diformylfuran in an excellent yield with high selectivity. The proposed mechanism, large-scale synthesis, and product separation were presented. This approach represents a straightforward and eco-friendly pathway, which can be applied in the large-scale production of 2,5-diformylfuran from fructose.
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http://dx.doi.org/10.1039/d0cc05582d | DOI Listing |
Chem Commun (Camb)
October 2020
Department of Organic Chemistry, Faculty of Chemistry, University of Science, Ho Chi Minh City, 721337, Vietnam. and Vietnam National University-Ho Chi Minh City (VNU-HCM), 721337, Vietnam.
Chemistry
June 2019
Department of Chemistry and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universitat Autònoma de Barcelona, 08193, Bellaterra (Cerdanyola del Vallès), Spain.
A highly enantioselective catalytic method for the synthesis of quaternary α-trifluoromethyl derivatives of 3-oxo esters is described. The reaction uses lanthanum(III) triflate and chiral PyBOX-type C -symmetric ligands to generate intermediate La complexes that incorporate an enolate moiety of the starting 3-oxo ester and the trifluoromethylation transfer reagent. The enantioselectivity of the reaction stems from the efficient blockage of one of the prochiral faces of the La enolate by one unit of the C -symmetric ligand.
View Article and Find Full Text PDFOrg Lett
April 2014
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, 812-8582, Japan.
Lanthanum trifluoromethanesulfonate is an effective single-component catalyst for synthesizing a variety of amides directly from esters and amines under mild conditions. Highly selective amidation of esters and amines, as well as catalyst-controlled amidation of esters, demonstrated the effectiveness of the catalyst system.
View Article and Find Full Text PDFJ Phys Chem B
July 2013
Department of Chemistry, Swedish University of Agricultural Sciences, P.O. Box 7015, SE-750 07 Uppsala, Sweden.
The coordination chemistry and the volumetric properties of three representative lanthanoid(III) ions--lanthanum(III), gadolinium(III), and lutetium(III)--have been studied in three amide solvents with gradually increasing spatial demand upon coordination: N,N-dimethylformamide (dmf) < N,N-dimethylacetamide (dma) < N,N-dimethylpropionamide (dmp). Large angle X-ray scattering (LAXS) and EXAFS have been used to determine the structure of the solvated lanthanoid(III) ions in solution, further supplemented with a crystallographic study on octakis(N,N-dimethylacetamide)lanthanum(III) triflate, [La(dma)8](CF3SO3)3. The selection of ions and solvents allows an estimate of the steric congestion effects on the resulting coordination number, CN, ranging from nine for lanthanum(III) ions in dmf to seven for the smaller lutetium(III) ion in space-demanding dma.
View Article and Find Full Text PDFJ Am Chem Soc
May 2010
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, USA.
Reaction screening of nucleophilic reaction partners for addition to N-diphenylphosphinylimines employing lanthanum(III) triflate as a catalyst and trifluoroacetic anhydride (TFAA) as an activator is reported. A number of tandem processes leading to novel chemotypes including aza-Prins/intramolecular Friedel-Crafts annulations have been identified, and both reaction scope and mechanism further investigated.
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