103-37-7Relevant articles and documents
Visible-light-initiated manganese-catalyzed Giese addition of unactivated alkyl iodides to electron-poor olefins
Dong, Jianyang,Wang, Xiaochen,Wang, Zhen,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
, p. 11707 - 11710 (2019)
Herein, we report a mild protocol for direct visible-light-initiated Giese addition of unactivated alkyl iodides to electron-poor olefins (Michael acceptors) with catalysis by decacarbonyl dimanganese, Mn2(CO)10, an inexpensive earth-abundant-metal catalyst. This protocol is compatible with a wide array of sensitive functional groups and has a broad substrate scope with regard to both the alkyl iodide and the Michael acceptor.
Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone
Wang, Song,Chang, Qian-Qian,Shawgi, Nazar,Li, San-Xi,Zhang, Lin-Nan
, p. 538 - 544 (2016)
A heterogeneous polyvinylpolypyrrolidone supported Br?nsted acidic catalyst ([PVPP-BS]HSO4) was used to synthesize butyrate in this paper. The prepared catalysts were characterized by FT-IR, TG, and FESEM and their catalytic activity in butyric acid esterification with benzyl alcohol was investigated. The influencing factors such as the amount of catalyst, reaction temperature, and reaction time were carefully studied. Under the optimized condition with the butyric acid to benzyl alcohol mole ratio of 1 : 1.2 and the reaction temperature of 130°C, the yield of benzyl butyrate reached 96.8 % within 4 h in the presence of 8 mass % of catalyst. Moreover, the catalyst could be reused six times without noticeable drop in activity. This catalyst was also used to synthesize other kinds of butyrates achieving the butyrate yield above 90 %.
N, O-ligand accelerated zinc-catalyzed transesterification of alcohols with vinyl esters
Mino, Takashi,Hasegawa, Tae,Shirae, Yoshiaki,Sakamoto, Masami,Fujita, Tsutomu
, p. 4389 - 4396 (2007)
N-Phenyldiethanolamine (1f) is an efficient ligand for zinc-catalyzed transesterification of alcohols with vinyl acetate (R3 = Me) at room temperature. In the case of using other vinyl esters (R3 = Et, n-Pr, Ph), the corresponding products were easily obtained in the presence of pyridine-type ligand 2 instead of aminoalcohol 1f.
Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA
Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
, p. 3666 - 3669 (2015)
Aromatic and aliphatic aldehydes are simply converted into esters by an efficient oxidative esterification carried out under mild conditions. The aldehydes are converted in situ into their corresponding acyl chlorides, which are then reacted with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols and phenols. A variety of esters are obtained in high yields.
The combine use of ultrasound and lipase immobilized on co-polymer matrix for efficient biocatalytic application studies
Badgujar, Kirtikumar Chandulal,Bhanage, Bhalchandra Mahadeo
, p. 255 - 264 (2015)
In this work, we have investigated the combine use of ultrasound and lipase (Pseudomonas cepacia: PCL) immobilized on co-polymer of polyvinyl alcohol (PVA) and chitosan (CHI) for biocatalytic applications. Initially, we have screened different free and immobilized biocatalysts to find-out the robust biocatalyst. The immobilized biocatalyst PVA:CHI:PCL (5:5:2.5) worked as a robust biocatalyst to provide superior conversion (99%) for the synthesis of model ultrasound assisted reaction. Subsequently, various reaction parameters were optimized in details to obtain the higher yield. Besides this, developed biocatalytic protocol was used to synthesize various industrially important butyrate compounds which provided excellent conversion of 99% under ultrasonic conditions. The developed biocatalyst showed excellent recyclability upto studied five cycles under ultrasonic condition. The immobilized PVA:CHI:PCL biocatalyst displayed 2.4 folds higher activity as compared to free lipases in ultrasonic condition. Moreover, PVA:CHI:PCL biocatalyst in ultrasound media showed 4.5 folds higher activity as compared to free lipases in conventional media. The energy assessment was performed which demonstrated feasibility of combine use of immobilization and ultrasonication to carry out efficient biocatalytic process.
Efficient Enzymatic Preparation of Flavor Esters in Water
Perdomo, Igor Chiarelli,Gianolio, Stefania,Pinto, Andrea,Romano, Diego,Contente, Martina Letizia,Paradisi, Francesca,Molinari, Francesco
, p. 6517 - 6522 (2019)
A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.
Selective Hydride-Mediated Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds Using 6
Mahoney, Wayne S.,Brestensky, Donna M.,Sryker, Jeffrey M.
, p. 291 - 293 (1988)
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Graphite oxide as an efficient solid reagent for esterification reactions
Mirza-Aghayan, Maryam,Rahimifard, Mahshid,Boukherroub, Rabah
, p. 859 - 864 (2014)
Esterification of organic acids with alcohols under mild conditions in high yields using graphite oxide, a readily available and inexpensive material, as an effective reagent is described.
Solvent stability study with thermodynamic analysis and superior biocatalytic activity of Burkholderia cepacia lipase immobilized on biocompatible hybrid matrix of poly(vinyl alcohol) and hypromellose
Badgujar, Kirtikumar C.,Bhanage, Bhalchandra M.
, p. 14808 - 14819 (2014)
In the present study, we have synthesized a biocompatible hybrid carrier of hypromellose (HY) and poly(vinyl alcohol) (PVA) for immobilization of Burkholderia cepacia lipase (BCL). The immobilized biocatalyst HY:-PVA:BCL was subjected to determination of half-life time (τ) and deactivation rate constant (KD) in various organic solvents. Biocatalyst showed higher τ-value in a nonpolar solvent like cyclohexane (822 h) as compared to that of a polar solvent such as acetone (347 h), which signifies better compatibility of biocatalyst in the nonpolar solvents. Furthermore, the KD-value was found to be less in cyclohexane (0.843 × 10-3) as compared to acetone (1.997 × 10-3), indicating better stability in the nonpolar solvents. Immobilized-BCL (35 mg) was sufficient to achieve 99% conversion of phenethyl butyrate (natural constituent of essential oils and has wide industrial applications) using phenethyl alcohol (2 mmol) and vinyl butyrate (6 mmol) at 44 °C in 3 h. The activation energy (Ea) was found to be lower for immobilized-BCL than crude-BCL, indicating better catalytic e fficiency of immobilized lipase BCL. The immobilized-BCL reported 6-fold superior biocatalytic activity and 8 times recyclability as compared to crude-BCL. Improved catalytic activity of immobilized enzyme in nonpolar media was also supported by thermodynamic activation parameters such as enthalpy (ΔH?), entropy (ΔS?) and Gibb 's free energy (ΔG?) study, which showed that phenethyl butyrate synthesis catalyzed by immobilized-BCL was feasible as compared to crude-BCL. The present work explains a thermodynamic investigation and superior biocatalytic activity for phenethyl butyrate synthesis using biocompatible immobilized HY:PVA:BCL in nonaqueous media for the first time. (Graph Presented).
Benzyne-Mediated Esterification Reaction
Li, Yang,Shi, Jiarong,Zhao, Jinlong
supporting information, p. 7274 - 7278 (2021/10/01)
A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.
Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond
Chen, Xuanxiao,Gouverneur, Véronique,Hell, Sandrine M.,Meyer, Claudio F.,Ortalli, Sebastiano,Sap, Jeroen B. I.
, p. 12149 - 12155 (2021/09/28)
A process for the direct hydrofluoromethylation of alkenes is reported for the first time. This straighforward silyl radical-mediated reaction utilises CH2FI as a non-ozone depleting reagent, traditionally used in electrophilic, nucleophilic and carbene-type chemistry, but not as a CH2F radical source. By circumventing the challenges associated with the high reduction potential of CH2FI being closer to CH3I than CF3I, and harnessing instead the favourable bond dissociation energy of the C-I bond, we demonstrate that feedstock electron-deficient alkenes are converted into products resulting from net hydrofluoromethylation with the intervention of (Me3Si)3SiH under blue LED activation. This deceptively simple yet powerful methodology was extended to a range of (halo)methyl radical precursors including ICH2I, ICH2Br, ICH2Cl, and CHBr2F, as well as CH3I itself; this latter reagent therefore enables direct hydromethylation. This versatile chemistry was applied to18F-,13C-, and D-labelled reagents as well as complex biologically relevant alkenes, providing facile access to more than fifty products for applications in medicinal chemistry and positron emission tomography.
