33342-22-2Relevant academic research and scientific papers
Asymmetric hydrogenation of disubstituted furans
Wysocki, Jedrzej,Ortega, Nuria,Glorius, Frank
supporting information, p. 8751 - 8755 (2014/08/18)
An enantioselective hydrogenation of disubstituted furans has been developed by using a chiral ruthenium catalyst with N-heterocyclic carbene ligands. This reaction converts furans into valuable enantioenriched disubstituted tetrahydrofurans.
Fast and efficient 18F-labeling by [18F]fluorophenylazocarboxylic esters
Fehler, Stefanie K.,Maschauer, Simone,Hcfling, Sarah B.,Bartuschat, Amelie L.,Tschammer, Nuska,Hubner, Harald,Gmeiner, Peter,Prante, Olaf,Heinrich, Markus R.
supporting information, p. 370 - 375 (2014/04/03)
Introduction of [18F]fluoride ion into the aromatic core of phenylazocarboxylic esters was achieved in only 30 seconds, with radiochemical yields of up to 95% (85(±10) %). For labeling purposes, the resulting 18F-substituted azoester can be further converted in radical-arylation reactions to give biaryls, or in substitutions at its carbonyl unit to produce azocarboxamides.
A C-H borylation approach to suzuki-miyaura coupling of typically unstable 2-heteroaryl and polyfluorophenyl boronates
Robbins, Daniel W.,Hartwig, John F.
supporting information; experimental part, p. 4266 - 4269 (2012/10/08)
A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.
Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation
Pridmore, Simon J.,Slatford, Paul A.,Taylor, James E.,Whittlesey, Michael K.,Williams, Jonathan M.J.
supporting information; experimental part, p. 8981 - 8986 (2009/12/27)
Alkyne-1,4-diols are readily available substrates which are isomerised to 1,4-diketones using Ru(PPh3)3(CO)H2/xantphos as a catalyst. In situ cyclisation into furans, pyrroles and pyridazines has been achieved under suitable conditions.
2,5-Disubstituted furans from 1,4-alkynediols
Pridmore, Simon J.,Slatford, Paul A.,Williams, Jonathan M.J.
, p. 5111 - 5114 (2008/02/09)
1,4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)3(CO)H2 with Xantphos at 1 mol % loading.
Ruthenium-catalysed conversion of 1,4-alkynediols into pyrroles
Pridmore, Simon J.,Slatford, Paul A.,Daniel, Aurélie,Whittlesey, Michael K.,Williams, Jonathan M.J.
, p. 5115 - 5120 (2008/02/09)
Various 1,2,5-substituted pyrroles have been synthesised from 1,4-alkynediols using a ruthenium catalysed isomerisation to give the corresponding 1,4-dicarbonyl compounds, which undergo in situ cyclisation to pyrroles in the presence of amine.
1,4-Carbonylative addition of arylboronic acids to methyl vinyl ketone: a new synthetic tool for rapid furan and pyrrole synthesis
Chochois, Hélène,Sauthier, Mathieu,Maerten, Eddy,Castanet, Yves,Mortreux, André
, p. 11740 - 11746 (2007/10/03)
The rhodium catalysed 1,4-carbonylative addition of arylboronic acids to methyl vinyl ketone under carbon monoxide pressure was studied. High yields of 1,4-diketones were obtained using a catalytic system formed from Rh(COD)2BF4 (COD=1,5-cyclooctadiene) and triphenylphosphine even at very low catalyst loading (0.02 mol %). A short synthetic procedure combining this carbonylation reaction with a subsequent cyclisation step affords pyrroles or furans.
