34740-23-3Relevant academic research and scientific papers
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 (2006)
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.
Synchronized C?H activations at proximate dinuclear Pd2+ sites on silicotungstate for oxidative C?C coupling
Ramineni, Kishore,Liu, Kairui,Zhang, Cheng,Chen, Xuke,Hou, Guangjin,Gao, Pan,Balaga, Ravi,Marri, Mahender Reddy,Yan, Peifang,Guan, Xian,Xia, Zhi,Janik, Michael J.,Zhang, Z. Conrad
, p. 3455 - 3465 (2021)
Carbon?carbon (C?C) coupling is critically important in organic synthesis. Direct C?C coupling to replace two C?H bonds is preferred over coupling of two prefunctionalized C?intermediates but is synthetically challenging. While such coupling is feasible through homogeneous catalysis, the mechanism regarding how the two C?H bonds are activated and coupled by heterogeneous active metal atoms remains not well understood. This work demonstrates the need for a proximate metal?metal dimer site to facilitate heterogeneously catalyzed C?C coupling reactions. We demonstrate that dinuclear Pd2+ sites in (Pd2+)2-silicotungstate (Pd2ST) catalyzed oxidative C?C coupling of 2-methylfuran by O2 through synchronized double C?H activations under ambient conditions, selectively producing 5,5′-dimethyl-2,2′-bifuran (DMBF). Mononuclear Pd2+ ions in Pd H ST and H ST are not active. The 13C NMR and DRIFT spectroscopies of adsorbed 13CO, combined with DFT and theoretical 13C NMR calculations, determined that dinuclear Pd2+ ions are separated by ～3.5 ? on Pd2ST and 3.1 ? in the Pd2+-C(=O)-Pd2+ complex. XRD and TEM are used to confirm that the most active Pd2ST/SiO2 catalyst has near monolayer dispersion. 29Si MAS NMR is used to confirm the presence of the silicotungstate structure after calcination. The original silicotungstate Keggin structure is maintained after the Pd2ST/SiO2 is calcined.
PREPARATION AND USE OF BIFURAN AND BIPHENYL DICARBOXYLIC ACIDS, ALCOHOLS, AND ESTERS
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Paragraph 0036, (2019/11/04)
A process for producing bifuran and/or biphenyl dicarboxylic acids, alcohols, and/or esters comprises reacting one or more furanyl compounds having the formula (I), where each R1 is independently selected from the group consisting of -H, -CH3, -CHO, -CH2OH, -COOH or -COOR2, where R2 is an alkyl group having from 1 to 20 carbon atoms, in the presence of a first catalyst to produce a reaction product comprising a bifuran compound having the formula (II).
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.
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.
Photochemical carbon skeletal rearrangement of the Baylis-Hillman products: β-C-H activation leading to furans
Matsumoto, Shoji,Mikami, Koichi
, p. 469 - 470 (2007/10/03)
Furan ring formation was found in photochemical reaction of the methyl ether of the Baylis-Hillman products. This reaction proceeds via β-C-H activation of the photo-excited carbonyl compounds.
The Photochemistry of α,β-Acetylenic Ketones. II. Formation of Furan Derivatives
Nishio, Takehiko,Nakata, Hiroyuki,Omote, Yoshimori
, p. 1011 - 1013 (2007/10/02)
The phochemical reactions of α,β-acetylenic ketones have been examined.Irradiation of 1-p-substituted phenyl-2-propyn-1-ones 2-4 in primary alcohols gave 2,5-disubstituted furans 2a-4c.The formation of furans can be explained in terms of cyclization, foll
Reactions with Monohydrazones of Dicarbonyl Compounds, X. 2-(Dimethylhydrazono)propanal as a Reagent for the Synthesis of 1,4-Diketones
Mayring, Lothar,Severin, Theodor
, p. 3863 - 3877 (2007/10/02)
Monohydrazones 7 of unsaturated 1,4-diketones can be prepared by the reaction of methylene-active ketones 1a-x with 2-(dimethylhydrazono)propanal (5a).From these products unsaturated (8) and saturated 1,4-diketones (9) are obtained in high yield.Reduction
