Synthesis of α-Cyanocinnamaldehydes from Acrylonitrile and Benzaldehydes Catalyzed by Pd(OAc)2/HPMoV/FeCl3/O2 System

Maeda, Satomi; Horikawa, Norihide; Obora, Yasushi; Ishii, Yasutaka

doi:10.1021/jo9021293

Cited by 10 publications

(6 citation statements)

References 24 publications

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“…100 A similar reaction at the ipso position was also carried out with benzaldehyde in place of benzene where ethanol was added to form the diacetal and FeCl 3 was used as a Lewis acid cocatalyst, Scheme 10. 101 More generally, using a similar reaction protocol, acrylates can be reacted with aliphatic aldehydes to yield 3-carboxy furans in a ring closing reaction that is thought to proceed through allylic palladation of an in situ formed acetal according to Scheme 11. 102 Under very similar reaction condition acrylate esters, preferably iso-butyl acrylate, can be trisannelated to yield the 1,3,5-tricarboxy esters of benzene in fair yields.…”

Section: Coupling Reactions With Alkenesmentioning

confidence: 99%

“…The benzene was oxidized with acrylonitrile catalyzed by Pd(OAc) 2/ H 3+ x PV x Mo 12‑ x O 40 /O 2 to yield the corresponding cinnamonitriles . A similar reaction at the ipso position was also carried out with benzaldehyde in place of benzene where ethanol was added to form the diacetal and FeCl 3 was used as a Lewis acid cocatalyst, Scheme …”

Section: Palladium(ii) Catalyzed Reactionsmentioning

confidence: 99%

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Dioxygen in Polyoxometalate Mediated Reactions

2017

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In this review article, we consider the use of molecular oxygen in reactions mediated by polyoxometalates. Polyoxometalates are anionic metal oxide clusters of a variety of structures that are soluble in liquid phases and therefore amenable to homogeneous catalytic transformations. Often, they are active for electron transfer oxidations of a myriad of substrates and upon reduction can be reoxidized by molecular oxygen. For example, the phosphovanadomolybdate, HPVMoO, can oxidize Pd(0) thereby enabling aerobic reactions catalyzed by Pd and HPVMoO. In a similar vein, polyoxometalates can stabilize metal nanoparticles, leading to additional transformations. Furthermore, electron transfer oxidation of other substrates such as halides and sulfur-containing compounds is possible. More uniquely, HPVMoO and its analogues can mediate electron transfer-oxygen transfer reactions where oxygen atoms are transferred from the polyoxometalate to the substrate. This unique property has enabled correspondingly unique transformations involving carbon-carbon, carbon-hydrogen, and carbon-metal bond activation. The pathway for the reoxidation of vanadomolybdates with O appears to be an inner-sphere reaction, but the oxidation of one-electron reduced polyoxotungstates has been shown through intensive research to be an outer-sphere reaction. Beyond electron transfer and electron transfer-oxygen transfer aerobic transformations, there a few examples of apparent dioxygenase activity where both oxygen atoms are donated to a substrate.

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Section: Coupling Reactions With Alkenesmentioning

confidence: 99%

Section: Palladium(ii) Catalyzed Reactionsmentioning

confidence: 99%

Dioxygen in Polyoxometalate Mediated Reactions

2017

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“…Compound 1 was readily prepared in one step by condensation of coumarinyl aldehyde 4 with 3,3-diethoxypropionitrile 5 in the presence of FeCl 3 (Scheme ) . The synthesis of control compound 2 was based on a reported procedure .…”

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confidence: 99%

Rational Design of a Highly Reactive Ratiometric Fluorescent Probe for Cyanide

et al. 2011

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“…The first step corresponds to a condensation between 3,3-diethoxypropanenitrile 5 and dialdehydes 3 or 4 in the presence of FeCl 3 as catalyst. 33 Bisformylacrylonitrile derivatives 6 and 7 were obtained in 28-30% yields after hydrolysis. Finally condensation reactions with pentafluoroaniline 8 were carried out at room temperature in dichloromethane and in the presence of a small amount of P 2 O 5 to give the target molecules 1 and 2 in 30-35% yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties

et al. 2013

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Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties † ‡ Chady Moussallem, Magali Allain, Fre ´de ´ric Gohier and Pierre Fre `re*The synthesis, the electronic properties and the solid state arrangements of conjugated systems associating pentafluorophenyl units linked via azomethine bonds to a central 2,5-di(cyanovinyl)thiophene or furan moieties have been investigated. The crystal structures of the two compounds are analyzed in terms of intermolecular interactions involving hydrogen and halogen bonding, p-p stacking and donor-acceptor interactions. Both structures reveal similar p-stacking of the molecules with nevertheless a more compact packing mode for the furan derivative. Moreover this structure is stabilized by several FÁ Á ÁF interactions between the columns of molecules. By contrast for the thiophene derivative, the structure requires the insertion of CH 2 Cl 2 to be stabilized via ClÁ Á ÁF interactions.

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Synthesis of α-Cyanocinnamaldehydes from Acrylonitrile and Benzaldehydes Catalyzed by Pd(OAc)₂/HPMoV/FeCl₃/O₂ System

Cited by 10 publications

References 24 publications

Dioxygen in Polyoxometalate Mediated Reactions

Dioxygen in Polyoxometalate Mediated Reactions

Rational Design of a Highly Reactive Ratiometric Fluorescent Probe for Cyanide

Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties

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