122-72-5Relevant academic research and scientific papers
Oxidation and reduction of various substrates over a Pd(II) containing post-synthesis metal organic framework
Hossain, Shahin,Jin, Myung-Jong,Park, Ji-Hoon,Yingjie, Qian,Yang, Da-Ae
, p. 122 - 125 (2013)
A palladium containing metal-organic framework (MOF) compound has been synthesized from MOF, (Zn4O)3(BDC-NH2) 3(BTB)4 through Schiff base condensation reaction and complexation of Pd(II). Pd-MOF was found to be an effective heterogeneous catalyst for the oxidation and hydrogenation of various substrates under mild reaction conditions. This catalytic method is highly active and shape selective. Graphical Abstract: [InlineMediaObject not available: see fulltext.]
Synthesis of acetoxyamides and acetates by zinc bromide assisted cleavage of Merrifield resin-bound ethers
Li, Wen-Ren,Yo, Ying-Chih
, p. 9085 - 9089 (1999)
A new method for the synthesis of acetoxyamides and acetates using Merrifield resin is described. The method uses zinc bromide to promote the conversion of Merrifield resin-bound ethers to acetates under ambient conditions. The cleavage products obtained are of high yields and chemical purity.
Nanomagnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica as a novel nanomagnetic phase-transfer catalyst for the aqueous synthesis of benzyl acetates and thiocyanates
Davarpanah, Jamal,Kiasat, Ali Reza
, p. 98 - 103 (2013)
Abstract Nanomagnetic double-charged diazoniabicyclo[2.2.2]octane dichloride silica hybrid (Fe3O4@SiO2/DABCO) was used as an efficient and magnetically recoverable phase-transfer catalyst (PTC) for nucleophilic substitution reactions of benzyl halides for the synthesis of benzyl acetates and thiocyanates in good to excellent yields at 100 C in water. No evidence for the formation of by-products, for example, isothiocyanate or benzyl alcohol was observed and the products were obtained in pure form without further purification. The catalyst was easily separated with the assistance of an external magnetic field from the reaction mixture and reused for several consecutive runs without significant loss of its catalytic efficiency.
Cerium ammonium nitrate (CAN) for mild and efficient reagent to remove hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines
Fujioka, Hiromichi,Hirose, Hideki,Ohba, Yusuke,Murai, Kenichi,Nakahara, Kenji,Kita, Yasuyuki
, p. 625 - 637 (2007)
Cerium ammonium nitrate (CAN) removed hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines to produce alcohols and amines in good yields. Especially, removal of the 2-hydroxyethyl ethers from C2-symmetric diols, chiral 2,3-butanediol and chiral hydrobenzoin, was very useful for asymmetric syntheses using C2-symmetric diols. The reactions using dual abilities of CAN, i.e.,?the ability for removal of the 2-hydroxyethyl unit and the ability for acetal hydrolysis by a single electron transfer, were also achieved successfully. The reaction conditions were very mild and efficient, and many functional groups, which can be affected under normal conditions, were unaffected during the reaction.
Ruthenium-catalysed domino hydroformylation-hydrogenation-esterification of olefins
Beller, Matthias,Dühren, Ricarda,Franke, Robert,Jackstell, Ralf,Kucmierczyk, Peter,Schneider, Carolin
, p. 5777 - 5780 (2021/09/10)
A novel catalytic domino reductive hydroformylation-esterification of olefins is reported. The optimal protocol makes use of an inexpensive Ru carbonyl catalyst and uses acetic acid as both solvent and reactant. In general, moderate to good yields are obtained using aliphatic or aromatic olefins including industrially relevant di-isobutene. This atom-efficient catalytic transformation provides straightforward access to various acetate esters from unfunctionalized olefins.
Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols
Koszelewski, Dominik,Brodzka, Anna,Madej, Arleta,Trzepizur, Damian,Ostaszewski, Ryszard
, p. 6331 - 6342 (2021/05/06)
Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.
Second-Generation meta-Phenolsulfonic Acid-Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification
Hu, Hao,Ota, Hajime,Baek, Heeyoel,Shinohara, Kenta,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
supporting information, p. 160 - 163 (2020/01/02)
A second-generation m-phenolsulfonic acid-formaldehyde resin (PAFR II) catalyst was prepared by condensation polymerization of sodium m-phenolsulfonate and paraformaldehyde in an aqueous H2SO4 solution. This reusable, robust acid resin catalyst was improved in both catalytic activity and stability, maintaining the characteristics of the previous generation catalyst (p-phenolsulfonic acid-formaldehyde resin). PAFR II was applied in the batchwise and continuous-flow direct esterification without water removal and provided higher product yields in continuous-flow esterification than any other commercial ion-exchanged acid catalyst tested.
Asymmetric synthesis of 1,2-fluorohydrin: Iridium catalyzed hydrogenation of fluorinated allylic alcohol
Ponra, Sudipta,Yang, Jianping,Wu, Haibo,Rabten, Wangchuk,Andersson, Pher G.
, p. 11189 - 11194 (2020/11/04)
We have developed a simple protocol for the preparation of 1,2-fluorohydrin by asymmetric hydrogenation of fluorinated allylic alcohols using an efficient azabicyclo thiazole-phosphine iridium complex. The iridium-catalyzed asymmetric synthesis of chiral 1,2-fluorohydrin molecules was carried out at ambient temperature with operational simplicity, and scalability. This method was compatible with various aromatic, aliphatic, and heterocyclic fluorinated compounds as well as a variety of polyfluorinated compounds, providing the corresponding products in excellent yields and enantioselectivities. This journal is
METHOD FOR PRODUCING IODIDE ESTER COMPOUND
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Paragraph 0127-0129; 0148; 0150; 0166; 0168; 0181; 0183, (2020/03/25)
PROBLEM TO BE SOLVED: To provide a method for producing an iodide ester compound that makes it possible to obtain a target iodide ester compound in high yield with high regioselectivity for iodine introduction. SOLUTION: A method for producing an iodide ester compound includes an iodide forming step in which: in the presence of a porous material, an ester compound represented by the following formula (2), iodine (I2), and an iodine-based oxide are reacted with each other, an iodide ester compound represented by the following formula (3) is formed. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPO&INPIT
Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights
Mai, Binh Khanh,Koenigs, Rene M.,Nguyen, Thanh Vinh,Lyons, Demelza J.M.,Empel, Claire,Pace, Domenic P.,Dinh, An H.
, p. 12596 - 12606 (2020/11/18)
Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.
