- Solvent-free oxidation of straight-chain aliphatic primary alcohols by polymer-grafted vanadium complexes
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Oxidovanadium(IV) complexes [VO(tertacac)2] (1), [VO(dipd)2] (2), and [VO(phbd)2] (3) were synthesized by reacting [VO(acac)2] with 2,2,6,6-tetramethyl-3,5-hepatanedione, 1,3-diphenyl-1,3-propanedione, and 1-phenyl-1,3-butanedione, respectively. Imidazole-modified Merrifield resin was used for the heterogenization of complexes 1–3. During the process of heterogenization, the V4+ center in complex 2 converts into V5+, whereas the other two complexes 1 and 3 remain in the oxidovanadium(IV) state in the polymer matrix. Theoretically, calculated IPA values of 1–3 suggest that 2 is prone to oxidation compared with 1 and 3, which was also supported by the absence of EPR lines in 5. Polymer-supported complexes Ps-Im-[VIVO(tertacac)2] (4), Ps-Im-[VVO2(dipd)2] (5), and Ps-Im-[VIVO(phbd)2] (6) were applied for the solvent-free heterogenous oxidation of a series of straight-chain aliphatic alcohols in the presence of H2O2 at 60°C and showed excellent substrate conversion specially for the alcohols with fewer carbon atoms. Higher reaction temperature improves the substrate conversion significantly for the alcohols containing more carbon atoms such as 1-pentanol, 1-hexanol, and 1-heptanol while using optimized reaction conditions. However, alcohols with fewer carbon atoms seem less affected by reaction temperatures higher than the optimized temperature. A decreasing trend in the selectivity(%) of carboxylic acid was observed with increasing carbon atoms among the examined alcohols, whereas the selectivity towards aldehydes increased. The order of efficiency of the supported catalysts is 4 > 6 > 5 in terms of turnover frequency (TOF) values and substrate conversion, further supported by theoretical calculations.
- Chaudhary, Nikita,Haldar, Chanchal,Kachhap, Payal
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- Aerobic oxidation and oxidative esterification of alcohols through cooperative catalysis under metal-free conditions
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The ABNO@PMO-IL-Br material obtained by anchoring 9-azabicyclo[3.3.1]nonane-3-oneN-oxyl (keto-ABNO) within the mesopores of periodic mesoporous organosilica with bridged imidazolium groups is a robust bifunctional catalyst for the metal-free aerobic oxidation of numerous primary and secondary alcohols under oxygen balloon reaction conditions. The catalyst, furthermore, can be successfully employed in the first metal-free self-esterification of primary aliphatic alcohols affording valued esters.
- Karimi, Babak,Ghahremani, Mina,Vali, Hojatollah,Ciriminna, Rosaria,Pagliaro, Mario
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supporting information
p. 8897 - 8900
(2021/09/10)
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- Metal complex catalysts and method for catalytically reducing carboxylic acids
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The invention relates to a metal complex catalyst, which contains at least one of metal complexes with a chemical formula comprising a structural unit represented by a formula I. According to the invention, the center metal of the metal complex catalyst is iridium, and the metal complex catalyst is composed of pentamethylcyclopentadienyl, a bitetrahydropyrimidine ligand and proper coordination anions; the metal complex catalyst has activity on a carboxylic acid reduction reaction, and a carboxylic acid compound is reduced into an alcohol compound in the presence of hydrogen; and the method ismild in reaction condition, can be carried out at room temperature, and is good in catalytic performance and high in reduction product yield.
- -
-
Paragraph 0085-0144; 0153; 0154; 0167-0168; 0178-0179
(2020/06/20)
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- A robust NNP-type ruthenium (II) complex for alcohols dehydrogenation to esters and pyrroles
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A Ru (II) complex bearing pyridyl-based benzimidazole-phosphine tridentate NNP ligand was synthesized and structurally characterized by NMR, IR. The complex can efficiently and selectively catalyze the acceptorless dehydrogenation of primary alcohols to esters under relatively mild conditions and the synthesis of pyrroles by means of the reactions of secondary alcohols and β-amino alcohols through acceptorless deoxygenation condensation.
- Chai, Huining,Zhang, Guangyao,Tan, Weiqiang,Ma, Jiping
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- Aerobic Self-Esterification of Alcohols Assisted by Mesoporous Manganese and Cobalt Oxide
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Aerobic self-esterification of primary alcohols catalyzed by mesoporous metal oxides (manganese and cobalt oxides) is reported under base and solvent free conditions. For a range of aliphatic alcohols, up to 90 % conversions to esters was achieved. The catalytic reaction is likewise applicable to neat aldehydes as substrates with yields of up to 86 %. High pressure batch reaction for ethanol to ethyl acetate led to 22 % yield. Isotope labeling studies indicated decarboxylation on the catalyst surface. Mechanistic and kinetic experiments implicate oxygen rebound and α-carbon removal as intermediate steps. Mesoporous cobalt oxide showed about 20 % higher catalytic activity compared to mesoporous manganese oxide.
- Moharreri, Ehsan,Biswas, Sourav,Deljoo, Bahareh,Kriz, David,Lim, Seyoung,Elliott, Sarah,Dissanayake, Shanka,Dabaghian, Marina,Aindow, Mark,Suib, Steven L.
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p. 3413 - 3422
(2019/08/01)
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- Oxidative esterification of primary alcohols at room temperature under aqueous medium
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Oxidative esterification of aliphatic primary alcohols with bromide and bromate couple in aqueous acidic medium at room temperature is reported with a wide range of substrate scope for both aliphatic and cyclic alcohols and obtained excellent yields of products.
- Reddy, N. Naresh Kumar,Ravi, Chitrakar,Adimurthy, Subbarayappa
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p. 1663 - 1670
(2018/06/15)
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- Cobalt-Catalyzed Acceptorless Dehydrogenative Coupling of Primary Alcohols to Esters
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A novel catalytic system with a tripodal cobalt complex is developed for efficiently converting primary alcohols to esters. KOtBu is found essential to the transformation. A preliminary mechanistic study suggests a plausible reaction route that involves an initial Co-catalyzed dehydrogenation of alcohol to aldehyde, followed by a Tishchenko-type pathway to ester mediated by KOtBu.
- Paudel, Keshav,Pandey, Bedraj,Xu, Shi,Taylor, Daniela K.,Tyer, David L.,Torres, Claudia Lopez,Gallagher, Sky,Kong, Lin,Ding, Keying
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supporting information
p. 4478 - 4481
(2018/08/09)
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- A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine
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An efficient method for the oxidation of alcohols to aldehydes or ketones in a two-phase CH2Cl2/NaHCO3 (aq.) system, using iodine and catalytic amounts of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl and 2,4,6-trimethylpyridine, was developed. The performance of the method was demonstrated by the selective oxidation of 37 variously substituted alcohols in ≥90% yield, including the gram-scale synthesis of the important chemical 2,5-diformylfuran from biomass-derived 5-hydroxylmethylfurfural.
- Kashparova, Vera P.,Klushin, Victor A.,Zhukova, Irina Yu.,Kashparov, Igor S.,Chernysheva, Daria V.,Il'chibaeva, Irina B.,Smirnova, Nina V.,Kagan, Efim Sh.,Chernyshev, Victor M.
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supporting information
p. 3517 - 3521
(2017/10/05)
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- Solvent- and base-free synthesis of wax esters from fatty acid methyl esters by consecutive one-pot, two-step catalysis
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The one-pot, two-step synthesis of wax esters was successfully conducted by consecutive homogeneous ruthenium-catalysed hydrogenation-dehydrogenation reactions of fatty acid methyl esters, in the absence of solvent and of base additive. Under optimized conditions, excellent conversion and selectivity were reached. Furthermore, physicochemical investigations revealed that the resulting compounds display properties similar to benchmark commercial products extracted from natural sources of lesser availability compared to the herein considered bioresources, making this chemical route very promising regarding further potential industrial implementation.
- Nguyen,Raffa,Morin,Desset,Capet,Nardello-Rataj,Dumeignil,Gauvin
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supporting information
p. 5665 - 5673
(2017/12/06)
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- Dehydrogenative coupling of alcohols to esters on a silica polyamine composite by immobilized PNN and PONOP pincer complexes of ruthenium
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Heterogenization of catalytically important homogeneous catalysts on solid supports has become an expanding area of research. PNN and PONOP ruthenium pincer complexes were immobilized on a silica poly(allylamine) composite, BP-1 by a two-step Mannich reaction. The complexes on BP-1 were characterized by solid state NMR, FT-IR, elemental analysis, and metal digestion studies. Model solution experiments were carried out to determine the site of electrophilic substitution on the pyridine ring of the pincer complexes and revealed substitution in both the meta- and para-position. The catalytic reactivity of immobilized (PNN)RuH(Cl)(CO) and (PONOP)RuH(Cl)(CO) on BP-1 was studied for the dehydrogenative coupling of alcohols to esters with the liberation of H2. Moderate to good ester yields were realized with both immobilized systems without using the base required for the homogeneous reaction and also in the presence of KOH. The homogeneous model reactions required a base for ester formation. The amine functionality on BP-1 served as the base to generate the active pincer catalyst on the BP-1 surface. Both immobilized catalysts were recycled for multiple alcohol reaction cycles. Four-step control experiments were carried out using an alcohol and both immobilized systems. The results revealed the heterogeneity of the alcohol catalysis by both BP-1-Ru-PNN and BP-1-Ru-PONOP systems. This study has opened a new catalytic methodology for reactions where base is required for catalyst activation, by using a solid support with basic functionality.
- Goni, Md Abdul,Rosenberg, Edward,Gobetto, Roberto,Chierotti, Michele
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p. 213 - 228
(2017/07/22)
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- Oxidative dimerization of alcohols in the presence of nitroxyl radical–iodine catalytic system
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Pyridine catalyzes oxidation of alcohols with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl–iodine catalytic system at room temperature. Symmetric esters are formed in good yields.
- Kashparova,Kashparov,Zhukova, I. Yu.,Astakhov,Ilchibaeva,Kagan, E. Sh.
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p. 2423 - 2426
(2016/12/24)
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- Regioselective Thiocarbonylation of Vinyl Arenes
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A palladium-catalyzed thiocarbonylation of styrene derivatives is reported for the first time. The combination of thiols as nucleophiles and a bidentate ligand ensures a unique reaction outcome with high regioselectivity toward the more valuable branched isomer and new reactivity. The ambient reaction conditions (temperature, catalyst loading) and the use of a CO surrogate render this transformation a useful method for the synthesis of thioesters from available feedstock. Various functional groups on arene and thiol substituents are tolerated by the system. Notably, challenging ortho-substituted styrenes are converted with unprecedentedly high regioselectivity.
- Hirschbeck, Vera,Gehrtz, Paul H.,Fleischer, Ivana
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supporting information
p. 16794 - 16799
(2017/01/10)
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- Highly efficient self-esterification of aliphatic alcohols using supported gold nanoparticles under mild conditions
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Long aliphatic esters were prepared by the one-step catalytic self-esterification of primary alcohols using molecular oxygen as a green oxidant and supported gold nanoparticles (Au NPs) as catalyst. This heterogeneous catalyst achieved high activity and selectivity in a wide range of less reactive straight-chain alcohols (C4-C12) at atmospheric pressure O2 and near ambient temperature (45?°C). Under optimised conditions, the catalyst with Au loading of 3?wt% achieved the highest catalytic activity and selectivity. The AuNP catalysts are efficient and readily recyclable. The finding of this study may inspire further studies on new efficient catalytic systems for a wide range of organic syntheses using supported AuNP catalysts.
- Wang, Fan,Xiao, Qi,Han, Pengfei,Sarina, Sarina,Zhu, Huaiyong
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- Primary alkanols: oxidative homocondensation in water and cross-condensation in methanol
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Water was used as a reaction medium and a reagent in oxidation of primary alkanols to dimeric esters and alkanoic acids using either molecular bromine or a hydrogen peroxide—hydrobromic acid mixture as the oxidants. The similar reaction in methanol produced methyl alkanoates.
- Nikishin,Sokova,Terent′ev,Kapustina
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p. 2845 - 2850
(2016/09/28)
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- Catalytic transformation of aliphatic alcohols to corresponding esters in o2 under neutral conditions using visible-light irradiation
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Selective oxidation of aliphatic alcohols under mild and base-free conditions is a challenging process for organic synthesis. Herein, we report a one-pot process for the direct oxidative esterification of aliphatic alcohols that is significantly enhanced by visible-light irradiation at ambient temperatures. The new methodology uses heterogenerous photocatalysts of gold-palladium alloy nanoparticles on a phosphate-modified hydrotalcite support and molecular oxygen as a benign oxidant. The alloy photocatalysts can absorb incident light, and the light-excited metal electrons on the surface of metal nanoparticles can activate the adsorbed reactant molecules. Tuning the light intensity and wavelength of the irradiation can remarkably change the reaction activity. Shorter wavelength light (550 nm) drives the reaction more efficiently than light of longer wavelength (e.g., 620 nm), especially at low temperatures. The phosphate-exchanged hydrotalcite support provides sufficient basicity (and buffer) for the catalytic reactions; thus, the addition of base is not required. The photocatalysts are efficient and readily recyclable. The findings reveal the first example of using "green" oxidants and light energy to drive direct oxidative esterification of aliphatic alcohols under base-free, mild conditions.
- Xiao, Qi,Liu, Zhe,Bo, Arixin,Zavahir, Sifani,Sarina, Sarina,Bottle, Steven,Riches, James D.,Zhu, Huaiyong
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p. 1956 - 1966
(2015/03/04)
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- Acceptorless dehydrogenative coupling of primary alcohols to esters by heterogeneous Pt catalysts
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Supported platinum catalysts have been studied for the acceptor-free dehydrogenative coupling of primary alcohols to esters in the liquid phase under solvent-free conditions in N2at 180 °C. The activity depends on the support material, and Pt-loaded SnO2(Pt/SnO2) gives the highest activity. Pt/SnO2shows higher activity than various transition metals (Ir, Re, Ru, Rh, Pd, Ag, Co, Ni, Cu) loaded on SnO2. The Pt/SnO2catalyst (1 mol%) selectively converted various primary alcohols to their corresponding esters in moderate to high isolated yield (53-91%). This is the first example of reusable heterogeneous catalysts for the acceptor-free dehydrogenative coupling of primary alcohols to esters under additive-free and solvent-free conditions. Mechanistic and infrared (IR) studies are also shown to discuss the reaction pathway and a possible role of the SnO2support as Lewis acid sites that activate carbonyl groups of adsorbed aldehyde intermediates.
- Moromi, Sondomoyee Konika,Hakim Siddiki,Ali, Md. Ayub,Kon, Kenichi,Shimizu, Ken-Ichi
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p. 3631 - 3635
(2015/02/05)
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- Well-defined iron catalysts for the acceptorless reversible dehydrogenation-hydrogenation of alcohols and ketones
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Acceptorless dehydrogenation of alcohols, an important organic transformation, was accomplished with well-defined and inexpensive iron-based catalysts supported by a cooperating PNP pincer ligand. Benzylic and aliphatic secondary alcohols were dehydrogenated to the corresponding ketones in good isolated yields upon release of dihydrogen. Primary alcohols were dehydrogenated to esters and lactones, respectively. Mixed primary/secondary diols were oxidized at the secondary alcohol moiety with good chemoselectivity. The mechanism of the reaction was investigated using both experiment and DFT calculations, and the crucial role of metal-ligand cooperativity in the reaction was elucidated. The iron complexes are also excellent catalysts for the hydrogenation of challenging ketone substrates at ambient temperature under mild H2 pressure, the reverse of secondary alcohol dehydrogenation.
- Chakraborty, Sumit,Lagaditis, Paraskevi O.,F?rster, Moritz,Bielinski, Elizabeth A.,Hazari, Nilay,Holthausen, Max C.,Jones, William D.,Schneider, Sven
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p. 3994 - 4003
(2015/01/16)
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- Efficient dimeric esterification of alcohols with NBS in water using l-proline as catalyst
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The L-proline-catalyzed oxidation of aliphatic primary alcohols with N-bromosuccimide (NBS) in water at room temperature to afford the corresponding dimeric esters in good to excellent yields was described. This pathway of dimeric esterification was proved to be very simple and environmentally friendly.
- Liu, Xiuhong,Wu, Jun,Shang, Zhicai
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experimental part
p. 75 - 83
(2011/11/05)
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- From esters to alcohols and back with ruthenium and osmium catalysts
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There and back again: Hydrogenation of esters and the reverse reaction of dehydrogenative coupling of alcohols are efficiently catalyzed by dimeric complexes of Ru and Os under neutral conditions. The Os dimer (see picture) is an outstanding catalyst for the hydrogenation of alkenoates and triglycerides, and allows production of fatty alcohols from olive oil. This complex converts ethanol into ethyl acetate and hydrogen under reflux. Copyright
- Spasyuk, Denis,Smith, Samantha,Gusev, Dmitry G.
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supporting information; experimental part
p. 2772 - 2775
(2012/05/20)
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- Selective oxidation of primary alkanols into the "symmetrical" esters with the H2O2-MBr-HCl system
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Oxidation of linear or branched primary alkanols with H2O 2-MBr (M = Li, Na, K)-HCl system in water affords the corresponding "symmetrical" esters in almost quantitative yield.
- Nikishin,Sokova,Kapustina
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experimental part
p. 310 - 312
(2011/11/05)
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- Oxidation of primary and secondary alkanols with the CeIII-LiBr- H2O2 system
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Action of a novel oxidation system, Ce(NO3)3? 6H2O (cat.)-LiBr (cat.)-H2O2 (stoichiometric oxidant) on primary aliphatic C6-C9 alcohols gives selectively esters, whereas secondary aliphatic C5-C9 alcohols are converted into ketones. Selectivity of these transformations is provided by slow addition of H2O2 to the other reactants.
- Kapustina,Sokova,Nikishin
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experimental part
p. 1284 - 1288
(2011/02/23)
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- Oxidation of alkanols into "symmetric" esters with the system Ce(SO4)2-LiBr
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A method for the synthesis of "symmetric" esters based on the oxidation of primary straight-and iso-chain aliphatic alcohols C6 -C11 with the system Ce(SO4)2-LiBr in water has been suggested.
- Nikishin,Sokova,Kapustina
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experimental part
p. 303 - 308
(2010/07/09)
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- Tishchenko reactions of aldehydes promoted by diisobutylaluminum hydride and its application to the macrocyclic lactone formation
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Aliphatic aldehydes react with catalytic amount of Dibal-H in n-pentane to give the corresponding Tishchenko products in good to excellent yields. On contrary, α-silyloxy aldehydes give α-silyloxy ketones via Oppenauer oxidation under similar condition. Tishchenko reaction of ω-alkene aldehydes followed by RCM and hydrogenation affords a convenient method to prepare the 11-37 membered macrocyclic lactones.
- Hon, Yung-Son,Wong, Ying-Chieh,Chang, Chun-Ping,Hsieh, Cheng-Han
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p. 11325 - 11340
(2008/03/12)
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- Solvent-free oxidation of aliphatic alcohols with ceric ammonium nitrate-lithium bromide system
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Esters are formed during the solvent-free oxidation of primary aliphatic C5-C9 alcohols with Ce(NH4)2(NO 3)6-LiBr, whereas secondary octan-2-ol gives a mixture of isomeric 1-and 3-bromooctan-2-ones.
- Kapustina,Sokova,Gasanov,Nikishin
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p. 1501 - 1506
(2008/09/19)
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- Remarkable reactivity of pyridinium chlorochromate adsorbed on neutral alumina under solvent-free conditions
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Pyridinium chlorochromate adsorbed on neutral alumina (PCC-Al2O3) under solvent-free conditions has been found to oxidize primary aliphatic alcohols to alkyl alkanoates whereas primary benzylic and primary allylic alcohols produce the corresponding aldehydes. Secondary aliphatic and aromatic alcohols produce ketones without isomerization and polymerization of double bonds, overoxidation and other side-reactions.
- Bhar, Sanjay,Chaudhuri, Subrata Kumar
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p. 3493 - 3498
(2007/10/03)
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- Catalytic processes of oxidation by hydrogen peroxide in the presence of Br2 or HBr. Mechanism and synthetic applications
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The mechanism and the synthetic applications for the oxidation of alcohols, ethers, and aldehydes by H2O2 catalyzed by Bf2 or Br- in a liquid two-phase system (aqueous and organic) are reported. Aliphatic and benzylic primary alcohols and ethers show an opposite behavior, which has been rationalized on the ground of the different electronic configurations of the intermediate alkyl (π-type) and acyl (σ-type) radicals and their influence on enthalpic and polar effects. A two-phase system is particularly useful also for an efficient benzylic bromination by Br2 or Br-; the substitution of the benzyl bromide by OH, OR, and OCOR regenerates Br-, which can be recycled. The evaluation of the relative reactivities of the involved substrates and intermediates has allowed to develop a variety of simple, facile, convenient, and selective syntheses of alcohols, aldehydes, ketones, esters, and benzyl bromides, which fulfill the conditions for practical applications.
- Amati, Alessandro,Dosualdo, Gabriele,Zhao, Lihua,Bravo, Anna,Fontana, Francesca,Minisci, Francesco,Bjorsvik, Hans-Rene
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p. 261 - 269
(2013/09/08)
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- A Convenient Preparation of Ketones by the Oxidation of Secondary Alcohols with Chromium(VI) Trioxide in Aprotic Solvent in the Presence of "Wet"-Aluminium Oxide
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The oxidation of aliphatic and alicyclic secondary alcohols with chromium(VI) trioxide in the presence of "wet"-aluminium oxide in hexane gave the corresponding ketones in excellent yields under mild conditions.
- Hirano, Masao,Nagasawa, Sonoko,Morimoto, Takashi
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p. 2857 - 2859
(2007/10/02)
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- Oxidation of Primary Alcohols to Methyl Esters Using tert-Butyl Hypochlorite, Pyridine and Methyl Alcohol
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When treated with tert-butyl hypochlorite, in the presence of pyridine and methyl alcohol, saturated aliphatic primary alcohols are oxidized to methyl esters in very high yields.Oxidation of benzylic alcohols, under the same conditions, yields a mixture of aldehydes and methyl esters.It appears that this reaction is a three-step process with an aldehyde and acyl chloride as the intermediates.Investigation of the relative rates of reaction reveals that benzyl alcohols are, as expected, oxidized faster than aliphatic alcohols, while the corresponding aldehydes show an opposite trend in reactivity.The reaction mechanism is proposed and the difference in the reactivity for aliphatic and benzylic aldehydes attributed to the stereoelectronic factors.
- Milovanovic, Jovan N.,Vasojevic, Miorad,Gojkovic, Svetislav
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p. 1231 - 1233
(2007/10/02)
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- The Dehydrogenation of Alcohols with Tris-(o-methoxyphenyl)carbenium Chloride.
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Heptan-1-ol, benzyl alcohol, and cyclohexanol are dehydrogenated by tris-(o-methoxyphenyl)carbenium chloride (2) in dichloromethane solution under mild conditions without concomitant formation of quinonoid adducts (6) (through the intermediacy of which part of the alcohols would be trapped and escape oxidation).The yields of the resulting benzaldehyde and cyclohexanone are good to excellent; but the yield of the saturated aldehyde heptanal is at best moderate.In contrast to benzaldehyde and cyclohexanone, heptanal is sensitive to the reagent (2) under the prevailing conditions, and is further transformed into mixtures of heptanoic acid, heptyl heptanoate and 2-pentylnon-2-enal.
- Huszthy, Peter,Lempert, Karoly,Simig, Gyula,Tamas, Jozsef,Hegedus-Vajda, Judit,Almasy, Attila
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p. 2524 - 2540
(2007/10/02)
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- HYDROFORMYLATION OF OLEFINS WITH PARAFORMALDEHYDE CATALYZED BY RHODIUM COMPLEXES
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The addition of formaldehyde to olefins is efficiently catalyzed by RhH2(O2COH)2 and gives the corresponding aldehydes in neutral solution.
- Okano, Tamon,Kobayashi, Teruyuki,Konishi, Hisatoshi,Kiji, Jitsuo
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p. 4967 - 4968
(2007/10/02)
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- PREPARATION D'ESTERS PAR DESHYDROGENATION D'ALCOOLS PRIMAIRES EN PHASE LIQUIDE CATALYSEE PAR L'OXYDE DE CUIVRE - OBSERVATIONS PRELIMINAIRES
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Linear primary alcohols with at least 7 carbon atoms are quite quantitatively transformed in esters, by CuO, at temperatures > 17O deg C, without air in liquid phase. Preponderant influence of carbon in position 2 is evidenced.In the same conditions lactones are obtained from diols, and benzylic alcohols undergoes, by hydride transfer, a disproportionation into toluene, benzaldehyde and water.
- Berthon, Bruno,Forestiere, Alain,Leleu, Gerard,Sillion, Bernard
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p. 4073 - 4076
(2007/10/02)
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