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Cas Database

122-78-1

122-78-1

Identification

  • Product Name:Phenylacetaldehyde

  • CAS Number: 122-78-1

  • EINECS:204-574-5

  • Molecular Weight:120.151

  • Molecular Formula: C8H8O

  • HS Code:29122990

  • Mol File:122-78-1.mol

Synonyms:Phenylacetic aldehyde;Phenylethanal;a-Phenylacetaldehyde;a-Tolualdehyde;a-Toluic aldehyde;Acetaldehyde,phenyl- (8CI);Benzylcarboxaldehyde;Hyacinthin;NSC 406309;Phenacetaldehyde;Benzeneacetaldehyde;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,FlammableF

  • Hazard Codes:Xn,F

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH317 May cause an allergic skin reaction

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Phenylacetaldehyde
  • Packaging:25g
  • Price:$ 333
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  • Manufacture/Brand:TRC
  • Product Description:Phenylacetaldehyde(90%Purity)
  • Packaging:100 g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Phenylacetaldehyde (40-55% in Diethyl Phthalate)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde ≥95%, FCC, FG
  • Packaging:10 kg
  • Price:$ 1080
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde ≥95%, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde ≥90%
  • Packaging:500ml
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde ≥95%, FCC, FG
  • Packaging:1 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde ≥95%, FCC, FG
  • Packaging:1kg-k
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde solution natural, 10 wt. % in ethanol, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Phenylacetaldehyde solution natural, 10 wt. % in ethanol, FG
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Relevant articles and documentsAll total 939 Articles be found

Structure and Unprecedented Reactivity of a Mononuclear Nonheme Cobalt(III) Iodosylbenzene Complex

Fukuzumi, Shunichi,Kim, Kyung Ha,Lee, Yong-Min,Nam, Wonwoo,Seo, Mi Sook,Shearer, Jason,Yang, Jindou

, p. 13581 - 13585 (2020)

A mononuclear nonheme cobalt(III) iodosylbenzene complex, [CoIII(TQA)(OIPh)(OH)]2+ (1), is synthesized and characterized structurally and spectroscopically. While 1 is a sluggish oxidant in oxidation reactions, it becomes a competent oxidant in oxygen atom transfer reactions, such as olefin epoxidation, in the presence of a small amount of proton. More interestingly, 1 shows a nucleophilic reactivity in aldehyde deformylation reaction, demonstrating that 1 has an amphoteric reactivity. Another interesting observation is that 1 can be used as an oxygen atom donor in the generation of high-valent metal-oxo complexes. To our knowledge, we present the first crystal structure of a CoIII iodosylbenzene complex and the unprecedented reactivity of metal-iodosylarene adduct.

-

Matsuda,Sugishita

, p. 1446,1449 (1962)

-

Selective isomerization of aryl substituted epoxides to aldehydes via iron Lewis acid catalysis

Picione, John,Mahmood, Syed J.,Gill, Andy,Hilliard, Marion,Hossain, M. Mahmun

, p. 2681 - 2684 (1998)

The iron Lewis acid [(η5-C5H5)Fe(CO)2(THF)]+BF4- (2) catalyzes the ring opening isomerization of aryl substituted epoxides (1) to aldehydes (3) in excellent yield.

Mechanism of Alkene Epoxidation by a Cytochrome P-450 Model. Effect of Additives

Razenberg, Johannes A. S. J.,Nolte, Roeland J. M.,Drenth, Wiendelt

, p. 277 - 279 (1986)

Alcohols and styrene change the kinetics and the mechanism of alkene epoxidation by the mono-oxygenase model (tetra-p-tolylporphinato)manganese(III) acetate-sodium hypochlorite.

REGIOSELECTIVITY OF OLEFIN OXIDATION BY IODOSOBENZENE CATALYZED BY METALLOPORPHYRINS: CONTROL BY THE CATALYST

Mansuy, Daniel,Leclaire, Jacques,Fontecave, Marc,Dansette, Patrick

, p. 2847 - 2857 (1984)

The regioselectivity of the oxidation of three monosubstituted olefins, 6-phenoxyhex-1-ene, hex-1-ene and styrene, by iodosobenzene in the presence of various Fe-, Mn- or Cr-tetraaryl-porphyrins, was studied.It was found that, besides epoxides, known products from such systems, allylic alcohols and aldehydes were formed, the latter not being derived from the corresponding epoxides.The relative importance of these reactions greatly depends upon both the metal and porphyrin constituents of the catalyst.More particularly, the competition between epoxidation and allylic hydroxylation can be efficiently controlled by non bonded interactions between the olefin and porphyrin substituents.No hydroxylation of the aromatic rings and no oxidative dealkylation of the ether function was detected.

Catalytic Hydrogenation of Styrene Oxide with Cationic Rhodium Complexes

Fujitsu, Hiroshi,Shirahama, Shinichi,Matsumura, Eiichi,Takeshita, Kenjiro,Mochida, Isao

, p. 2287 - 2290 (1981)

Catalytic hydrogenation of styrene oxide with cationic rhodium complexes was investigated to develop its selective conversion into the specific alcohol. β-Phenylethyl alcohol and phenylacetaldehyde were rather selectively produced without either α-phenylethyl alcohol or acetophenone through a selective antinormal fission of the epoxide ring.The catalytic activity and selectivity were found to depend strongly on the ligand, the activity for the formation of alcohol decreasing in the order, PEt3 > PMe3 PPh3 >> diphos.The highest yield, achieved by the PEt3 complex, reached as high as 82percent after 8 h of reaction.A possible mechanism was proposed to explain the selective formation of β-phenylethyl alcohol and the role of water as a cocatalyst in the catalytic hydrogenation.

New pathway for heterogenization of molecular catalysts by non-covalent interactions with carbon nanoreactors

Lebedeva, Maria A.,Chamberlain, Thomas W.,Schr?der, Martin,Khlobystov, Andrei N.

, p. 6461 - 6466 (2014)

A novel approach to heterogenization of catalytic molecules is demonstrated using the nanoscale graphitic step edges inside hollow graphitized carbon nanofibers (GNFs). The presence of the fullerene C60 moiety within a fullerene-salen CuII complex is essential for anchoring the catalyst within the GNF nanoreactor as demonstrated by comparison to the analogous catalyst complex without the fullerene group. The presence of the catalyst at the step edges of the GNFs is confirmed by high-resolution transmission electron microscopy (TEM) and energy-dispersive X-ray spectroscopy (EDX) with ultraviolet/visible (UV/vis) spectroscopy, demonstrating only negligible (ca. 3%) desorption of the fullerene-salen CuII complex from the GNFs into solution under typical reaction conditions. The catalyst immobilized in GNFs shows good catalytic activity and selectivity toward styrene epoxidation, comparable to the analogous catalyst in solution. Moreover, the fullerene-salen CuII complex in GNFs demonstrates excellent stability and recyclability because it can be readily separated from the reaction mixture and employed in multiple reaction cycles with minimal loss of activity, which is highly advantageous compared to catalysts not stabilized by the graphitic step edges that desorb rapidly from GNFs.

Controlled release of encapsulated bioactive volatiles by rupture of the capsule wall through the light-induced generation of a gas

Paret, Nicolas,Trachsel, Alain,Berthier, Damien L.,Herrmann, Andreas

, p. 2275 - 2279 (2015)

The encapsulation of photolabile 2-oxoacetates in core-shell microcapsules allows the light-induced, controlled release of bioactive compounds. On irradiation with UVA light these compounds degrade to generate an overpressure of gas inside the capsules, which expands or breaks the capsule wall. Headspace measurements confirmed the light-induced formation of CO and CO2 and the successful release of the bioactive compound, while optical microscopy demonstrated the formation of gas bubbles, the cleavage of the capsule wall, and the leakage of the oil phase out of the capsule. The efficiency of the delivery system depends on the structure of the 2-oxoacetate, the quantity used with respect to the thickness of the capsule wall, and the intensity of the irradiating UVA light.

Convenient method for the transformation of epoxide to aldehyde and acetonide mediated by Cr-PLM

Chareonsiriwat, Laddawan,Chavasiri, Warinthorn

, p. 257 - 267 (2017)

Chromium-pillared montmorillonite (Cr-PLM) could be synthesized and efficiently utilized for styrene oxide transformations. The target aldehyde product could be quantitatively achieved from the isomerization of styrene oxide by using 10 wt% of Cr-PLM under reflux temperature for 15 min. The acetonide product could be achieved in excellent yield from the reaction of styrene oxide and acetone by using 10 wt% of Cr-PLM under room temperature for 20 min. The catalyst could be recovered and reused at least five times without loss of activity.

Enhanced iron(III) corrole-catalyzed oxidations with iodobenzene diacetate: Synthetic and mechanistic investigations

Chen, Tse-Hong,Kwong, Ka Wai,Carver, Aaron,Luo, Weilong,Zhang, Rui

, p. 121 - 126 (2015)

The electron-deficient iron(III) corrole complex catalyzes the efficient oxidation of hydrocarbons using PhI(OAc)2 as an mild oxygen source. The catalyst stability against degradation was much enhanced owing to the mild oxidizing ability of PhI(OAc)2. Excellent selectivity and high catalytic efficiency (with up to 1400 TON) have been achieved in alkene epoxidations. This promising oxygen transfer process is mechanistically rationalized in terms of a putative high-valent iron(V)-oxo species as the active oxidant.

Synthesis, structural studies and catalytic activity of a series of dioxidomolybdenum(VI)-thiosemicarbazone complexes

Roy, Satabdi,Saswati,Lima, Sudhir,Dhaka, Sarita,Maurya, Mannar R.,Acharyya, Rama,Eagle, Cassandra,Dinda, Rupam

, p. 134 - 143 (2018)

Reaction of the thiosemicarbazone ligands, [4-(p-bromophenyl)thiosemicarbazone of salicylaldehyde (H2L1), 4-(p-X-phenyl)thiosemicarbazone of o-vanillin {X = F (H2L2), X = Cl (H2L3) and X = OMe (H2L4)}, 4-(p-bromophenyl)thiosemicarbazone of 5-bromosalicylaldehyde (H2L5), and 4-(p-chlorophenyl)thiosemicarbazone of o-hydroxynaphthaldehyde (H2L6)] with [MoO2(acac)2] afforded a series of new oxidomolybdenum(VI) complexes [Mo(VI)O2L1–6(solv)] (1–6) {where solv (solvent) = DMSO (1, 3, 5 & 6) and H2O (2 & 4)}. The molecular structures of 2 and 3 were determined by X-ray crystallography, demonstrating the dibasic tridentate behavior of ligands. The cyclic voltammogram pattern is similar for 1–6, which includes two irreversible reduction processes within the potential window ?0.71 to ?0.66 V and ?0.92 to ?0.85 V corresponding to the metal centered reduction from Mo(VI)/Mo(V) and Mo(V)/Mo(IV) respectively. Catalytic potential of 1–6 was tested for the oxidation of styrene and cyclohexene. The effect of various parameters such as the amount of catalyst, oxidant, NaHCO3, and solvent was checked to optimize the conditions for the best performance of the catalyst. 100% product selectivity for the formation of cyclohexene oxide from cyclohexene and ~98–99% product selectivity for the oxidation of styrene to styrene oxide was observed.

On the Mechanism of the Ruthenium-catalyzed β-methylation of Alcohols with Methanol

Kaithal, Akash,Schmitz, Marc,H?lscher, Markus,Leitner, Walter

, p. 781 - 787 (2020)

Selective β-methylation of alcohols with methanol has been recently described using a catalytic system comprising the ruthenium pincer complex [RuH(CO)(BH4)(HN(C2H4PPh2)2)]-(Ru-MACHO-BH) 1 and alcoholate bases as co-catalysts. Here we present a detailed mechanistic analysis for the mono-methylation of 1-phenyl-propane-1-ol 2 a as prototypical example. Several experimentally observed intermediates were localized as stable minima on the DFT-derived energy surface of the entire reaction network. The ruthenium complex [Ru(H)2(CO)(HN(C2H4PPh2)2)] I was inferred as the active species catalyzing the de-hydrogenation/re-hydrogenation of substrates and intermediates (“hydrogen borrowing”). The hydrogen-bonded alcohol adduct of this complex was identified as the lowest lying intermediate (TDI). The C?C bond formation results from a base-catalyzed aldol reaction comprising the transition state with the highest energy (TDTS). Experimentally determined Gibbs free activation barriers of 26.1 kcal/mol and 26.0 kcal/mol in methanol and toluene as solvents, respectively, are reflected well by the computed energy span of the complex reaction network (29.2 kcal/mol).

Activation of Nitrite Ion by Iron(III) Porphyrins. Stoichiometric Oxygen Transfer to Carbon, Nitrogen, Phosphorus, and Sulfur

Castro, Charles E.,O'Shea, Stephen K.

, p. 1922 - 1923 (1995)

-

Natural Abundance 2H Nuclear Magnetic Resonance Study of the Origin of 2-Phenylethanol and 2-Phenylethyl Acetate

Fronza, Giovanni,Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Zucchi, Gioia,et al.

, p. 439 - 443 (1995)

The site-specific natural abundance deuterium distribution of 2-phenylethanol (1) and 2-phenylethyl acetate (2) obtained through a variety of methods has been determined by 2H NMR spectroscopy.This technique provided a means of distinguishing between "natural" materials isolated from natural sources or obtained by biodegradation of L-phenylalanine and other products of petrochemical origin or obtained from natural L-phenylalanine through nonenzymic controlled chemical processes.Keywords: SNIF-NMR; aromas; 2-phenylethanol; 2-phenylethyl acetate; authentication

Synthesis of aldehydes from oxiranes using silica gel as reagent

Lemini,Ordonez,Perez-Flores,Cruz-Almanza

, p. 2695 - 2702 (1995)

The rearrangement of some 2-aryl monosubstituted and 2-aryl, 2-methyl disubstituted oxiranes to aldehydes using silica gel in very mild conditions is reported.

Nanoporous alumino- and borosilicate-mediated Meinwald rearrangement of epoxides

Davies, Thomas E.,Kondrat, Simon A.,Nowicka, Ewa,Kean, Joseline L.,Harris, Christopher M.,Socci, Joseph M.,Apperley, David C.,Taylor, Stuart H.,Graham, Andrew E.

, p. 17 - 24 (2015)

Nanoporous alumino- and borosilicate materials, produced using an evaporation-induced self-assembly approach (EISA), efficiently catalyse the Meinwald rearrangement of epoxides in dimethyl carbonate (DMC) to produce the corresponding carbonyl compounds in high yield and excellent selectivity.

-

Kabasakalian,P.,Townley,E.R.

, p. 2711 - 2716 (1962)

-

Co2+-exchanged MOR and 5A zeolites as efficient solid catalysts for the epoxidation of styrene with air

Zhou,Tang,Lu,Wei,Li,Xia

, p. 124 - 128 (2014)

Selective oxidation of alkenes with air to corresponding epoxides was performed over simple ion-exchanged Co-MOR and Co-5A. Among all transition metal ions-exchanged M-zeolites, both Co-MOR and Co-5A exhibited the highest activity at 363 K. Notably, for the epoxidation of styrene, α-pinene, α-methyl styrene and cyclooctene, Co-MOR obtained higher conversions than Co-5A, in agreement with the difference of pore sizes of both zeolitic materials. Recycling and control tests showed high durability of Co-MOR as a heterogeneous catalyst in our catalytic system.

Three New Polyoxoniobates Functioning as Different Oxidation Catalysts

Cui, Xiao-Bing,Li, Guanghua,Zhang, Ting-Ting

, p. 3191 - 3201 (2021)

Three new multifunctional isopolyniobates based on {Nb24O72}, namely, [Cu(en)2]9.75[Cu(en)2(H2O)]4[KNb24O72H9.25]2·36.5H2O (1), [Cu(en)2][Cu(en)2(H2O)]12[Cu(en)2(H2O)2]3[KNb24O72H7(H2O)2]2·99H2O (2), and [K(H2O)4][Cu(en)2(H2O)2]5[Cu(en)2(H2O)]8.25[Cu(en)2]2[K0.5Nb24O72H7.75]2·115.31H2O (3) (en = ethylenediamine), were obtained and characterized by IR, powder X-ray diffraction, single-crystal diffraction analysis, etc. Single-crystal analyses of the three compounds shows that all their clusters exhibit the same bowl-shaped structure, while the different transition metal complexes (TMCs) make compounds 1-3 show three entirely different packing structures. The catalytic properties of the three compounds as catalysts for Rhodamine B (RhB) photocatalytic degradation, styrene oxidation, and oxygen evolution reaction (OER) have been assessed, and all the compounds have good catalytic effects on the three different catalytic processes.

A Methylidene Group in the Phosphonic Acid Analogue of Phenylalanine Reverses the Enantiopreference of Binding to Phenylalanine Ammonia-Lyases

Bata, Zsófia,Qian, Renzhe,Roller, Alexander,Horak, Jeannie,Bencze, László Csaba,Paizs, Csaba,Hammerschmidt, Friedrich,Vértessy, Beáta G.,Poppe, László

, p. 2109 - 2120 (2017)

Aromatic amino acid ammonia-lyases and aromatic amino acid 2,3-aminomutases contain the post-translationally formed prosthetic 3,5-dihydro-4-methylidene-5H-imidazol-5-one (MIO) group. MIO enzymes catalyze the stereoselective synthesis of α- or β-amino acid enantiomers, making these chemical processes environmentally friendly and affordable. Characterization of novel inhibitors enables structural understanding of enzyme mechanism and recognizes promising herbicide candidates as well. The present study found that both enantiomers of the aminophosphonic acid analogue of the natural substrate phenylalanine and a novel derivative bearing a methylidene at the β-position inhibited phenylalanine ammonia-lyases (PAL), representing MIO enzymes. X-ray methods unambiguously determined the absolute configuration of all tested enantiomers during their synthesis. Enzyme kinetic measurements revealed the enantiomer of the methylidene-substituted substrate analogue as being a mirror image relation to the natural l-phenylalanine as the strongest inhibitor. Isothermal titration calorimetry (ITC) confirmed the binding constants and provided a detailed analysis of the thermodynamic driving forces of ligand binding. Molecular docking suggested that binding of the (R)- and (S)-enantiomers is possible by a mirror image packing. (Figure presented.).

-

Grigg et al.

, p. 1248 (1971)

-

Different morphologies of silver nanoparticles as catalysts for the selective oxidation of styrene in the gas phase

Chimentao,Kirm,Medina,Rodriguez,Cesteros,Salagre,Sueiras

, p. 846 - 847 (2004)

Silver nanoparticles of different morphologies were prepared using the polyol process and then dispersed on α-alumina. Catalysts were tested for the selective oxidation of styrene in the gas phase. Activity and selectivity were strongly dependent on the morphology of the silver nanoparticles.

A Convenient Synthesis of Aldehydes by Rearrangement of Cyclic Epoxides with Lithium Bromide on Alumina

Suga, Hisashi,Miyake, Hajimu

, p. 394 - 395 (1988)

Epoxides can be converted effectively to aldehydes by rearrangement with lithium bromide supported on alumina.In the case of the alicyclic epoxides, ring contracted cycloalkanecarbaldehydes can be formed.The conversion is achieved by gas-phase reaction or in toluene as solvent.

First catalysis by corrole metal complexes: Epoxidation, hydroxylation, and cyclopropanation

Gross, Zeev,Simkhovich, Liliya,Galili, Nitsa

, p. 599 - 600 (1999)

The first ever application of corroles shows that their metal complexes are good catalysts, almost as potent as the corresponding metalloporphyrins in the oxygenation of hydrocarbons by iodosylbenzene and superior for the cyclopropanation of olefins by carbenoids.

One-Pot Synthesis of N-tert-Butylsulfinylimines and Homoallylamine Derivatives from Epoxides

Lahosa, Alejandro,Foubelo, Francisco,Yus, Miguel

, p. 4067 - 4076 (2016)

The reaction of epoxides with tert-butanesulfinamide in the presence of a Lewis acid, such as erbium triflate or boron trifluoride–diethyl ether, in THF as solvent, under microwave or thermal activation, produces N-tert-butylsulfinylimines in reasonable yields. Aromatic and gem-disubstituted and trisubstituted alkyl epoxides performed better than mono-alkyl-substituted compounds. After imine formation, a subsequent indium-promoted allylation can be carried out in the same reaction flask in a single synthetic operation leading to homoallylamine derivatives with generally high yields.

Productive asymmetric styrene epoxidation based on a next generation electroenzymatic methodology

Ruinatscha, Reto,Dusny, Christian,Buehler, Katja,Schmid, Andreas

, p. 2505 - 2515 (2009)

We have established a novel and scalable methodology for the productive coupling of redox enzymes to reductive electrochemical cofactor regeneration relying on efficient mass transfer of the cofactor to the electron-delivering cathode. Proof of concept is

-

Hickinbottom,Hogg

, p. 4200,4203 (1954)

-

Organosilyl Iron Carbonyl Complexes: Synthesis and Reactivity towards Alkynes and Nitriles

Corriu, Robert J. P.,Moreau, Joel J. E.

, p. 278 - 279 (1980)

The di-iron complex 2, readily obtained from Fe(CO)5 and Ph2SiH2 under photochemical conditions, react with the alkynes to yield the new mono- and bi-metallic complexes (R = Ph, Me, or Et) and ; the former complexes convert nitriles into aldehydes via disylilated enamines.

Kinetics and mechanism of oxidation of neutral α-amino acids by sodium N-chloro-p-toluenesulfon-amide in acid medium

Rangappa,Manjunathaswamy,Raghavendra,Made Gowda

, p. 49 - 55 (2002)

Kinetics of oxidation of α-amino acids, glycine, valine, alanine, and phenylalanine, by sodium N-chloro-p-toluenesulfonamide or chloramine-T (CAT) has been investigated in HClO4 medium at 30°C. The rate shows first-order dependence on both CAT and amino acid concentrations and an inverse first-order on [H+]. The variation of ionic strength and the addition of p-toluenesulfonamide and Cl- ion had no effect on the reaction rate. Decrease of dielectric constant of the medium by increasing the MeOH content decreased the rate. Rate studies in D2O medium showed the inverse solvent-isotope effect of kD(2)O/kH(2)O = 0.50. Proton-inventory studies were carried out using H2O-D2O mixtures. The activation parameters have been computed. The proposed mechanism and the derived rate law are consistent with the observed kinetic data. An isokinetic relationship is observed with β = 323 K, indicating enthalpy as a controlling factor. The rate of oxidation increases in the following order: Gly Val Phe Ala.

-

Zakharkin,Khorlina

, p. 619,620 (1962)

-

Oxidation of alcohols by iodine in the presence of nitroxyl radicals generated electrochemically

Kagan,Kashparova,Zhukova,Kashparov

, p. 745 - 747 (2010)

Oxidation of primary and secondary alcohols in the two-phase system of methylene chloride-aqueous solution of sodium hydrocarbonate in the presence of the mediator system of potassium iodide-nitroxyl radical was studied. It is supposed that under these co

Two inorganic–organic hybrids based on a polyoxometalate: Structures, characterizations, and epoxidation of olefins

Shi, Zhuolin,Mei, Chongzhen,Niu, Guiqin,Han, Qiuxia

, p. 1460 - 1468 (2018)

Two new inorganic–organic hybrids, [Co3(bpdo)6(H2O)4Cl2][SiW12O40]·H2O (Co-SiW) and [Ni3(bpdo)6(H2O)4Cl2][SiW12O40]·H2O (Ni-SiW) (bpdo?=?4,4′-bis(pyridine-N-oxide)), were synthesized from the Keggin-type [SiW12O40] anion and Co(II) and Ni(II) under hydrothermal conditions, respectively, and characterized by elemental analyses, powder XRD, IR spectra, and single-crystal X-ray diffraction. The structural analysis indicates that the 1D chain is constructed from a POM-based half-cage as a secondary building block linked by bridging bpdo ligands. The zigzag chains further stack into a three-dimensional body with channels. The 3D network structure with amphiphilic cavities is shaped by electrostatic interactions through the planes, which has potential to allow molecules such as styrene and H2O2 ingress and egress. Both of the hybrids demonstrated catalytic activity for epoxidation of olefins, which was examined using styrene and aqueous hydrogen peroxide (30%) as oxidant in acetonitrile, along with Co-SiW and Ni-SiW in a heterogeneous manner at 60?°C. Moreover, the conversion of epoxidation reaction in a heterogeneous manner is close to that of homogeneous catalysis, while being conveniently recovered and steadily reused without change of catalyst structure after epoxidation reactions.

Epoxidation of alkenes with aqueous hydrogen peroxide and quaternary ammonium bicarbonate catalysts

Mielby, Jerrik,Kegnaes, Soren

, p. 1162 - 1165 (2013)

A range of solid and liquid catalysts containing bicarbonate anions were synthesised and tested for the epoxidation of alkenes with aqueous hydrogen peroxide. The combination of bicarbonate anions and quaternary ammonium cations opens up for new catalytic systems that can help to overcome challenges with catalyst separation and reuse. Graphical Abstract: [Figure not available: see fulltext.]

Hydrogen peroxide dependent monooxygenations by tricking the substrate recognition of cytochrome P450BSβ

Shoji, Osami,Fujishiro, Takashi,Nakajima, Hiroshi,Kim, Misa,Nagano, Shingo,Shiro, Yoshitsugu,Watanabe, Yoshihito

, p. 3656 - 3659 (2007)

(Figure Presented) Trick or treat: Cytochrome P450BSβ was transformed into a monooxygenase suitable for practical use by employing a simple substrate trick. The substrate specificity of P450BSβ was altered drastically by a decoy molecule, while its intrinsic advantage, the use of hydrogen peroxide, was retained. The catalytic activities and the enantioselectivity of the H2O2-P450BSβ system are highly dependent on the structure of the decoy molecule.

Novelties of combustion synthesized and functionalized solid superacid catalysts in selective isomerization of styrene oxide to 2-phenyl acetaldehyde

Yadav, Ganapati D.,Gawade, Bapu A.

, p. 145 - 152 (2013)

Combustion synthesis leads to very interesting characteristics to inorganic oxides which could be further modified to render them catalytic properties. Several new approaches were studied to make a novel superacidic sulfated zirconia called fuel lean sulfated zirconia (FLSZ), by combustion synthesis. FLSZ was fully characterized and used in a reaction of industrial relevance. The isomerization of styrene oxide to 2-phenyl acetaldehyde was studied by using several solid acid catalysts. 2-Phenyl acetaldehyde finds applications in the synthesis of fine chemicals, intermediates, speciality chemicals, flavors and fragrances. Among various catalysts studied FLSZ was found to give the best activity and selectivity to 2-phenyl acetaldehyde at 100 °C using cyclohexane as a solvent. Process parameters were optimized by conducting a systematic investigation. The kinetics of the reaction was also studied. The catalyst is robust, recyclable and found to be highly active and selective. The overall process is 100% atom economical, green and clean.

Cytochrome P-450 modelling oxygenation of olefins within the space-restricted cavity of iron 'BINAP porphyrin': Rate enhancement in the presence of imidazole

Naruta,Maruyama

, p. 4553 - 4556 (1987)

-

KINETICS AND MECHANISM OF THE OXIDATION OF α-AMINO ACIDS BY N-BROMOACETAMIDE

Bishnoi, Mangi Lal,Banerji, Kalyan K.

, p. 6047 - 6050 (1985)

The kinetics of the oxidation of eight α-amino acids by N-bromoacetamide have been studied in aqueous perchloric acid solution.The main products of the oxidation are the corresponding carbonyl compounds.The reaction is of first order with respect to the oxidant and the amino acid.The rate of oxidation decreases linearly with an increase in hydrogen ion concentration.The rate is decreased by the addition of acetamide.The oxidation of deuteriated glycine indicated the absence of a primary kinetic isotope effect.The reaction rate has been determined at different temperatures and activation parameters have been caculated.Hypobromous acid has been postulated as the reactive oxidizing species.A rate-determining reaction of the neutral amino acid and hypobromous acid to give an N-bromo derivative has been proposed.The slow step is followed by a fast decomposition of the N-bromo derivative to yield the ultimate product.

4,6-Diacetyl Resorcinol Based Vanadium(V) Complexes: Reactivity and Catalytic Applications

Maurya, Mannar R.,Jangra, Nancy,Avecilla, Fernando,Correia, Isabel

, p. 314 - 329 (2019)

Four ONO donor ligands are isolated from the condensation of 4,6-diacetyl resorcinol with isonicotinoyl hydrazide (H2dar-inh, I), nicotinoyl hydrazide (H2dar-nah, II), benzoyl hydrazide (H2dar-bhz, III), and 2-furoyl hydrazide (H2dar-fah, IV) on refluxing in MeOH. The reaction of in situ generated aqueous K[H2VVO4] with ligands I–IV at neutral pH gives complexes [K(H2O)2][VO2(dar-inh)] (1), [K(H2O)2][VO2(dar-nah)] (2), [K(H2O)2][VO2(dar-bhz)] (3), and [K(H2O)2][VO2(dar-fah)] (4), respectively. The reaction of [VIVO(acac)2] (acac = acetylacetonato) with these ligands (I–IV) under aerobic conditions in methanol yields oxidomethoxidovanadium(V) complexes [VO(OMe)(MeOH)(dar-inh)] (5), [VO(OMe)(MeOH)(dar-nah)] (6), [VO(OMe)(MeOH)(dar-bhz)] (7), and [VO(OMe)(MeOH)(dar-fah)] (8). All the isolated complexes are characterized by elemental, thermal, electrochemical, and spectroscopic techniques [FTIR, UV/Vis, NMR (1H, 13C and 51V NMR)], and single-crystal X-ray diffraction analysis (for 1, 6, 7, and 8). X-ray analysis confirms the coordination of the ligands through Ophenolate, Nazomethine, and Oenolate to the metal center. In the molecular structure of [K(H2O)(EtOH)][VVO2(dar-inh)] (abbreviated as 1a where one molecule of water is replaced by EtOH), water molecules act as bridges between two K+ ions and the complex shows a dimeric structure due to the presence of electrostatic interactions between V=O oxygen atoms with K+ ions. These complexes are active catalysts for the oxidative bromination of thymol in the presence of KBr, HClO4, and H2O2 and give 2-bromothymol, 4-bromothymol, and 2,4-dibromothymol as major products. Complexes 1–4 were also tested as catalysts for the epoxidation of various alkenes (namely styrene, cyclohexene, cis-cyclooctene, 1-hexene, 1-octene, cyclohexenone, and trans-stilbene) with H2O2 in the presence of NaHCO3 as promoter, giving the corresponding epoxides selectively.

Simple green dehydration in biphasic medium: Application to the synthesis of phenylacetaldehyde

Le Guenic, Sarah,Ceballos, Claire,Len, Christophe

, p. 72 - 77 (2016)

A highly efficient, simple and versatile acid catalyst is proposed for the selective acid dehydration of 1-phenylethan-1,2-diol to phenylacetaldehyde in water-CPME biphasic media under microwave irradiation. A high stability and recyclability of the catalyst is also observed under the investigated conditions.

Catalytic Oxidation of Styrene in the Presence of Square Planar Cobalt(III) Complexes of Polyanionic Chelating Ligands

Collins, Terrence J.,Ozaki, Shigeko,Richmond, Thomas G.

, p. 803 - 804 (1987)

Styrene has been catalytically oxidised in the presence of iodosoarenes and square planar cobalt(III) complexes of polyanionic chelating (PAC) ligands; possible intermediates in these oxygen atom transfer reactions include cobalt(V)-oxo complexes.

Controlled light-induced release of volatile aldehydes and ketones by photofragmentation of 2-oxo-(2-phenyl)acetates

Levrand, Barbara,Herrmann, Andreas

, p. 661 - 664 (2007)

The light-induced controlled release of fragrances from photolabile 2-oxo-(2-phenyl)acetates via Norrish Type II photofragmentation was evaluated by irradiation of the precursors in different solvents and on cotton in a typical fabric softener application. The desired photooxidation was found to work efficiently in water-based systems, and it tolerates the presence of oxygen. The formation of a certain amount of alcohol besides the desired aldehyde or ketone was attributed to further reaction of the photochemically released carbonyl compound, rather than to ester hydrolysis in an aqueous environment. Schweizerische Chemische Gesellschaft.

Chemical conversion of α-amino acids into α-keto acids by 4,5-epoxy-2-decenal

Zamora, Rosario,Navarro, Jose L.,Gallardo, Emerenciana,Hidalgo, Francisco J.

, p. 6101 - 6105 (2006)

The comparative formation of phenylalanine and phenylpyruvic acid in the reaction of 4,5-epoxy-2-decenal with phenylalanine was studied to determine whether epoyalkenals may also degrade amino acids without producing their decarboxylation. Both compounds were produced in the reaction to an extent that depended on the reaction pH, the amount of lipid oxidation product, and the reaction time and temperature. The optimum pH was 3 for producing both carbonyl derivatives, and the amount of both compounds increased linearly with the amount of epoxyalkenal present in the reaction mixture. In addition, phenylpyruvic acid was produced to a higher extent than phenylacetaldehyde at 37°C. However, at 60°C the degradation of phenylpyruvic acid was observed and phenylacetaldehyde was usually found to a higher extent than the α-keto acid in the overnight-incubated reaction mixtures. The degradation of phenylpyruvic acid produced benzaldehyde and phenylacetaldehyde. All these results suggest that epoxyalkenals can not only degrade amino acids by a Strecker-type mechanism but convert them into their corresponding α-keto acids. This new reaction may be an alternative chemical route for the formation in foods of α-keto acids, which can later participate in the generation of important amino acid-derived flavor compounds.

Synthesis of meta-substituted monodentate phosphinite ligands and implication in hydroformylation ?

Deshmukh, Satej S,Gaikwad, Shahaji R,Pandey, Swechchha,Mali, Pramod S,Chikkali, Samir H

, p. 1143 - 1152 (2017)

Abstract: Synthesis of meta-substituted phosphinite ligands 3,3′-(methoxyphosphanediyl)bis(N,N- diethylaniline) (4a) and methoxybis(3-methoxyphenyl)phosphane (4b), in high yields, has been demonstrated. Typical phosphorus chemical shift between 110–120 ppm, appearance of methoxy protons and corresponding carbon, as well as ESI-MS spectra unambiguously confirmed the existence of phosphinite ligands 4a and 4b. To demonstrate the synthetic usefulness of 4a and 4b, these ligands were tested in the rhodium catalyzed hydroformylation of 1-octene. The diethylamine substituted ligand 4a was found to be highly active, whereas 4b was less reactive but revealed slightly better regioselectivity of 62% under optimized conditions. Additionally, 4a and 4b were found to catalyze the hydroformylation of styrene, 1-undecenol and 1,1-disubstituted functional olefin, methyl methacrylate. Both the ligands displayed excellent conversion of styrene, and 4b revealed an excellent branch selectivity of 75%. Although 1-undecenol proved to be amenable to hydroformylation (85–90% conversion to aldehyde), both the ligands failed to discriminate between the linear and branched products. Substrate methyl methacrylate proved to be highly challenging and reduced conversion (between 33–42%) was observed under optimized conditions. Ligand 4a was found to be highly selective towards linear aldehyde (81% linear selectivity). Graphical Abstract: Synopsis Two step synthetic protocol to access meta-substituted monodentate phosphinite ligands 3,3′-(methoxyphosphanediyl)bis(N,N-diethylaniline) (4a) and methoxybis(3-methoxyphenyl)phosphane (4b) has been developed and the ligands have been fully characterized. Apart from catalyzing the hydroformylation of benchmark substrates 1-octene and styrene, 4a and 4b were found to catalyze the hydroformylation of 1-undecenol, a functional olefin and a highly challenging 1,1-disubstituted functional olefin methyl methacrylate. [Figure not available: see fulltext.].

Rapid and efficient protic ionic liquid-mediated pinacol rearrangements under microwave irradiation

Henderson, Luke C.,Byrne, Nolene

, p. 813 - 816 (2011)

Several protic ionic liquids were tested as potential mediators for pinacol rearrangements employing microwave irradiation. Using hydrobenzoin as a model substrate, the optimal conditions were found to be heating at 80°C for 5 min using H2SO4:triethylamine as the ionic liquid. A key feature of this reaction was to keep the microwave power low (20 W) to avoid ionic liquid degradation. Application of these conditions to triphenylethylene glycol gave rearrangement products in high yield and purity, while phenylethylene glycol and styrene oxide gave pinacol products that underwent a cascade aldol condensation. These conditions represent an efficient means by which pinacol rearrangements can be carried out while avoiding the use of strong Bronsted acids, high temperatures and extended reaction times. The Royal Society of Chemistry.

Flash Photolytic Decarbonylation and Ring-Opening of 2-(N-(Pentafluorophenyl)amino)-3-phenylcyclopropenone. Isomerization of the Resulting Ynamine to a Ketenimine, Hydration of the Ketenimine, and Hydrolysis of the Enamine Produced by Ring-Opening

Chiang,Grant,Guo,Kresge,Paine

, p. 5363 - 5370 (1997)

Flash photolysis of 2-(N-(pentafluorophenyl)amino)-3-phenylcyclopropenone, 4, in aqueous solution was found to produce N-(pentafluorophenyl)phenylethynamine, 3, by the expected photodecarbonylation reaction and also 2-phenyl-3-(N-(pentafluorophenyl)amino)acrylic acid, 5, by an apparently unprecedented photochemical ring-opening process. The ynamine underwent rapid isomerization to N-(pentafluorophenyl)phenylketenimine, 9, by an acid-catalyzed route that involves rate- determining proton transfer to the β-carbon atom of the ynamine and also by a base-catalyzed route involving equilibrium ionization of the N-H bond of the ynamine to give an ynamide ion followed by rate-determining β-carbon protonation of this ion. Saturation of the base catalysis allowed determination of the acidity constant of the ynamine; the result, pQa = 10.23, makes this amine a remarkably strong nitrogen acid. Hydration of the ketenimine 9 gave N-(pentafluorophenyl)phenylacetamide, 6, as the ultimate product produced by this reaction route, and hydrolysis of the aminoacrylic acid 5 gave pentafluoroaniline, 7, and 2-phenylformylacetic acid, 10, which underwent decarboxylation to phenylacetaldehyde, 8, as the ultimate products of this route.

Intensification and economic and ecological assessment of a biocatalytic oxyfunctionalization process

Kuhn, Daniel,Kholiq, Muhammad Abdul,Heinzle, Elmar,Buehler, Bruno,Schmid, Andreas

, p. 815 - 827 (2010)

Bio-based processes are commonly accepted to be environmentally preferable to chemical alternatives. Reasons include high selectivities, the avoidance of heavy metals, and mild reaction conditions. However, ecological benefits and economic viability have to be verified in each case. Oxygenases are a very attractive enzyme class, allowing selective oxyfunctionalization by introduction of molecular oxygen into hydrocarbons at optical purities unparalleled by traditional chemical methods. Here, styrene monooxygenase from Pseudomonas sp. strain VLB120 was used in recombinant Escherichia coli for the production of enantiopure (S)-styrene oxide from styrene. Substrate and product toxicity was attenuated using a two-liquid phase system with bis(2-ethylhexyl)phthalate as organic carrier solvent. By maintaining previously reported productivities for a longer time period, product concentrations were doubled to 36.3 g L tot-1 making it one of the most productive biocatalytic oxyfunctionalization processes. This biotransformation was incorporated along with an appropriate upstream and downstream processing into a complete process scheme and compared with chemical process alternatives. Ecological assessment showed the bioprocess to be superior to two chemical process alternatives and slightly inferior to the third one, with solvent use being the most critical factor. However, the bioprocess performed best in terms of production costs ($10.2 kg-1). This study underlines the importance of a detailed ecological and economic assessment of bioprocesses to verify their sustainability and to identify weak points with respect to environmental and/or economical sustainability.

-

Naves

, p. 319 (1967)

-

Intermolecular Electrophilic Addition of Epoxides to Alkenes: [3+2] Cycloadditions Catalyzed by Lewis Acids

Shuler, William G.,Combee, Logan A.,Falk, Isaac D.,Hilinski, Michael K.

, p. 3335 - 3338 (2016)

Described are the first examples of intermolecular electrophilic additions of epoxides to alkenes, which proceed through a classic cationic mechanism initiated by epoxide C–O bond cleavage. Treatment of styrene oxides and either styrenes or dienes with a variety of Lewis-acidic triflate salts generates tetrahydrofurans as products of [3+2] cycloaddition in moderate to good yields (up to 71 %). Careful choice of catalyst and reaction conditions favors the desired intermolecular reaction over epoxide degradation without requiring additional reagents or additives. The reaction proceeds diastereoselectively and provides only one regioisomer of the product. Additional highlights include inexpensive precursors, mild conditions, short reaction times, low catalyst loading, and scalability.

Highly efficient Meinwald rearrangement reactions of epoxides catalyzed by copper tetrafluoroborate

Robinson, Mathew W.C.,Pillinger, Kathryn S.,Graham, Andrew E.

, p. 5919 - 5921 (2006)

Epoxides undergo a highly efficient and selective rearrangement in the presence of catalytic quantities of copper tetrafluoroborate to give carbonyl compounds in excellent yields. The low toxicity and ease of handling of this reagent make it an attractive alternative to the more corrosive Lewis acids frequently employed.

Oxidation of L-phenylalanine by diperiodatoargentate(III) in aqueous alkaline medium. A Mechanistic approach

Lamani,Veeresh,Nandibewoor

, p. 2215 - 2222 (2009)

The kinetics of oxidation of L-phenylalanine (L-Phe) by diperiodatoargentate(III) (DPA) in alkaline medium at a constant ionic strength of 0.25 mol/dm-3 has been studied spectrophotometrically. The reaction between DPA and L-phenylalanine in alkaline medium exhibits 1: 1 stoichiometry (L-phenylalanine: DPA). The reaction shows first order in [DPA] and has less than unit order dependence each in both [L-Phe] and [Alkali] and retarding effect of [IO 4 - ] under the reaction conditions. The active species of DPA is understood to be as monoperiodatoargentate(III) (MPA). The reaction is shown to proceed via a MPA-L-Phe complex, which decomposes in a rate-determining step to give intermediates followed by a fast step to give the products. The products were identified by spot and spectroscopic studies. The reaction constants involved in the different steps of the mechanisms were calculated. The activation parameters with respect to slow step of the mechanism were computed and discussed. The thermodynamic quantities were also determined for the reaction.

Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant

Fernandes, Rodney A.,Kumar, Praveen,Yadav, Sandhya S.

, p. 427 - 443 (2022/01/20)

This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(iii) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(iii) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.

Direct synthesis of 1,3-dithiolanes from terminal alkynes: Via visible light photoredox catalysis

Bhat, Ramakrishna G.,Dharpure, Pankaj D.,Khade, Vikas V.,Thube, Archana S.

supporting information, p. 1315 - 1319 (2022/02/21)

A visible light-mediated, metal-free, regioselective dihydrothionation of terminal aromatic as well as heteroaromatic alkynes has been achieved using Eosin Y as a photoredox catalyst at room temperature. The protocol gives direct access to different 1,3-dithiolanes under neutral and mild reaction conditions without the use of any base or additives. The electron-donating, electron-withdrawing and electron-deactivating groups tolerated the photocatalytic reaction conditions. The control experiments, cyclic voltammetry, and Stern-Volmer experiment were carried out to gain an insight into the mechanistic pathway. The protocol proved to be scalable at the gram level and also for practicality the deprotection of 1,3-dithiolanes has been demonstrated. The method uses clean energy under sustainable conditions. This journal is

One-Pot Bioelectrocatalytic Conversion of Chemically Inert Hydrocarbons to Imines

Chen, Hui,Tang, Tianhua,Malapit, Christian A.,Lee, Yoo Seok,Prater, Matthew B.,Weliwatte, N. Samali,Minteer, Shelley D.

supporting information, p. 4047 - 4056 (2022/02/10)

Petroleum hydrocarbons are our major energy source and an important feedstock for the chemical industry. With the exception of combustion, the deep conversion of chemically inert hydrocarbons to more valuable chemicals is of considerable interest. However, two challenges hinder this conversion. One is the regioselective activation of inert carbon-hydrogen (C-H) bonds. The other is designing a pathway to realize this complicated conversion. In response to the two challenges, a multistep bioelectrocatalytic system was developed to realize the one-pot deep conversion from heptane to N-heptylhepan-1-imine under mild conditions. First, in this enzymatic cascade, a bioelectrocatalytic C-H bond oxyfunctionalization step based on alkane hydroxylase (alkB) was applied to regioselectively convert heptane to 1-heptanol. By integrating subsequent alcohol oxidation and bioelectrocatalytic reductive amination steps based on an engineered choline oxidase (AcCO6) and a reductive aminase (NfRedAm), the generated 1-heptanol was successfully converted to N-heptylhepan-1-imine. The electrochemical architecture provided sufficient electrons to drive the bioelectrocatalytic C-H bond oxyfunctionalization and reductive amination steps with neutral red (NR) as electron mediator. The highest concentration of N-heptylhepan-1-imine achieved was 0.67 mM with a Faradaic efficiency of 45% for C-H bond oxyfunctionalization and 70% for reductive amination. Hexane, octane, and ethylbenzene were also successfully converted to the corresponding imines. Via regioselective C-H bond oxyfunctionalization, intermediate oxidation, and reductive amination, the bioelectrocatalytic hydrocarbon deep conversion system successfully realized the challenging conversion from inert hydrocarbons to imines that would have been impossible by using organic synthesis methods and provided a new methodology for the comprehensive conversion and utilization of inert hydrocarbons.

Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride

Azeez, Sadaf,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri

supporting information, p. 2048 - 2053 (2022/03/31)

A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.

Copper-Photocatalyzed Hydrosilylation of Alkynes and Alkenes under Continuous Flow

Zhong, Mingbing,Pannecoucke, Xavier,Jubault, Philippe,Poisson, Thomas

, p. 11818 - 11822 (2021/07/10)

Herein, the photocatalytic hydrosilylation of alkynes and alkenes under continuous flow conditions is described. By using 0.2 mol % of the developed [Cu(dmp)(XantphosTEPD)]PF6 under blue LEDs irradiation, a large panel of alkenes and alkynes was hydrosilylated in good to excellent yields with a large functional group tolerance. The mechanism of the reaction was studied, and a plausible scenario was suggested.

Process route upstream and downstream products

Process route

1-methoxy-4-(3-phenyl-1-propen-1-yl)benzene
35856-81-6,20442-74-4

1-methoxy-4-(3-phenyl-1-propen-1-yl)benzene

phenylacetaldehyde
122-78-1

phenylacetaldehyde

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
Conditions Yield
bei der Ozonolyse;
Conditions
Conditions Yield
With ammonium peroxydisulfate; copper diacetate; sodium acetate; In water; acetonitrile; at 100 ℃; Yield given. Further byproducts given. Yields of byproduct given;
Conditions
Conditions Yield
With ammonium peroxydisulfate; copper diacetate; In water; acetonitrile; at 100 ℃; Yield given. Further byproducts given. Yields of byproduct given;
Conditions
Conditions Yield
With trimethylamine-N-oxide; In dimethyl sulfoxide; for 1h; Ambient temperature;
83%
17%
β-styrylmagnesium bromide
30094-01-0,35672-47-0,56516-81-5

β-styrylmagnesium bromide

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

phenylacetaldehyde
122-78-1

phenylacetaldehyde

7-chloro-3-phenyl-1H-indole
124608-85-1

7-chloro-3-phenyl-1H-indole

Conditions
Conditions Yield
In tetrahydrofuran; at -40 ℃;
44%
phenylacetylene
536-74-3

phenylacetylene

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

2-phenylethanol
60-12-8

2-phenylethanol

phenylacetaldehyde
122-78-1

phenylacetaldehyde

acetophenone
98-86-2

acetophenone

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With monoaluminum phosphate; zinc(II) tetrahydroborate; In 1,2-dimethoxyethane; for 1h; Product distribution; Ambient temperature; other reagents; product selectivity;
β-(p-nitrophenylthio)-styrene
128183-94-8

β-(p-nitrophenylthio)-styrene

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

phenylacetaldehyde
122-78-1

phenylacetaldehyde

Conditions
Conditions Yield
With perchloric acid; ammonium vanadate; acetic acid; at 19.85 ℃; for 36h; Thermodynamic data; Rate constant; Kinetics; ΔH(excit.); ΔS(excit.); var. conc. of reactants and solvent; var. temp.;
diethyl ether
60-29-7,927820-24-4

diethyl ether

phosphorus pentachloride
10026-13-8,874483-75-7

phosphorus pentachloride

α-chloro-2',4'-dimethyl-chalcone oxime

α-chloro-2',4'-dimethyl-chalcone oxime

ammonia
7664-41-7

ammonia

phenylacetaldehyde
122-78-1

phenylacetaldehyde

2,4-dimethyl-benzoic acid
611-01-8

2,4-dimethyl-benzoic acid

Conditions
Conditions Yield
Erhitzen des Reaktionsprodukts mit wss. NaOH;
N-(1-deoxy-D-fructos-1-yl)-L-phenylalanine
71887-77-9

N-(1-deoxy-D-fructos-1-yl)-L-phenylalanine

3-phenylpyridine
1008-88-4

3-phenylpyridine

3,5-diphenylpyridine
92-07-9

3,5-diphenylpyridine

1-N-(2-Phenylethyl)aminonaphthalene
65021-64-9

1-N-(2-Phenylethyl)aminonaphthalene

phenylacetaldehyde
122-78-1

phenylacetaldehyde

1-amino-naphthalene
134-32-7

1-amino-naphthalene

1-(N-phenethyl-N-methyl)naphthaleneamine

1-(N-phenethyl-N-methyl)naphthaleneamine

Conditions
Conditions Yield
at 250 ℃; for 0.00555556h; Product distribution; Mechanism; var. temperatures; unsubstituted phenylalanine;
Conditions
Conditions Yield
With sodium hydroxide; dihydrogen peroxide; benzo[1,3,2]dioxaborole; bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; BABAR-Phos; In tetrahydrofuran; at 24.85 ℃; for 1h; Further Variations:; Catalysts; Product distribution;

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