112-42-5Relevant articles and documents
Hydrogenation reactions using scCO2 as a solvent in microchannel reactors
Kobayashi, Juta,Mori, Yuichiro,Kobayashi, Shu
, p. 2567 - 2568 (2005)
We have developed an effective microfluidic system for hydrogenation reactions in ScCO2; the reactions proceeded very rapidly (within 1 second), by making the best use of ScCO2 and utilizing the large specific interfacial area of the microchannel reactor, and high reaction productivity was attained in each channel. The Royal Society of Chemistry 2005.
Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
Bricout, Herve,Leonard, Estelle,Len, Christophe,Landy, David,Hapiot, Frederic,Monflier, Eric
, p. 1479 - 1484 (2012)
In this study, we showed that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji-Trost reaction). The RAME-β-CD/phosphane supramolecular interactions helped explain the catalytic results. The presence of RAME-β-CD in the aqueous compartment improved the phosphane-based aggregate dynamics. The exchanges between the hydrophobic substrate-containing aggregate core and the catalyst-containing aqueous phase were then greatly favored, resulting in an increase in the catalytic performances.
Convenient synthesis of new amphiphilic triphenylphosphine analogues for aqueous biphasic catalysis
Caron, Laurent,Canipelle, Micha?l,Tilloy, Sébastien,Bricout, Hervé,Monflier, Eric
, p. 8837 - 8840 (2001)
The synthesis of three triphenylphosphine analogues with phenyl groups replaced by (4-tert-butyl)phenyl and (3-sulfonato)phenyl group is described. The surface-active properties of these new compounds are reported. The catalytic activities obtained with these phosphines in the palladium-catalyzed cleavage of undecyl allyl carbonate were up to 24000 times higher than those observed with trisulfonated triphenylphosphine, the ligand typically used in biphasic catalysis. One of these catalysts can be recovered six times without loss of catalytic activity.
Ditopic cyclodextrin-based receptors: New perspectives in aqueous organometallic catalysis
Six, Natacha,Menuel, Stephane,Bricout, Herve,Hapiot, Frederic,Monflier, Eric
, p. 1467 - 1475 (2010)
The mass transfer properties of mono- and ditopic β-cyclodextrin-based receptors have been evaluated in a biphasic palladium-catalyzed Tsuji-Trost reaction and compared to one of the best mass-transfer promoters, namely the randomly methylated β-cyclodextrin. While monotopic receptors appeared to be poor mass-transfer promoters of long alkyl chain allyl carbonates or urethanes, cooperative effects have been evidenced with ditopic cyclodextrin-based receptors, opening new perspectives in aqueous organometallic catalysis.
Amphiphilic photo-isomerisable phosphanes for aqueous organometallic catalysis
Bricout, Herve,Banaszak, Estelle,Len, Christophe,Hapiot, Frederic,Monflier, Eric
, p. 7813 - 7815 (2010)
Water-soluble phosphanes were tagged with a light-responding diazo group. Upon UV exposure, the diazo-isomerisation led to phosphane morphology change, resulting in an increase in the reaction rate of an aqueous palladium-catalysed cleavage reaction. The Royal Society of Chemistry.
Chemically modified β-cyclodextrins: Efficient supramolecular carriers for the biphasic hydrogenation of water-insoluble aldehydes
Monflier, Eric,Tilloy, Sebastien,Castanet, Yves,Mortreux, Andre
, p. 2959 - 2960 (1998)
Hydrogenation of water-insoluble aldehydes can be achieved in high yields in a genuine two-phase system by using a recoverable catalytic system composed of a water-soluble ruthenium/triphenylphosphine trisulfonate complex and a suitable chemically modified β-cyclodextrin.
Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes
Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 8313 - 8320 (2021/03/08)
Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.
Selective hydroboration of equilibrating allylic azides
Liu, Ruzhang,Xu, Jun,Zhang, Yuanyuan
supporting information, p. 8913 - 8916 (2021/09/13)
The iridium(i)-catalyzed hydroboration of equilibrating allylic azides is reported to provide only the anti-Markovnikov product of alk-1-ene isomers in good yields and with good functional group tolerance.
Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols
Casnati, Alessandra,Lichosyt, Dawid,Lainer, Bruno,Veth, Lukas,Dydio, Pawe?
supporting information, p. 3502 - 3506 (2021/05/10)
One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).