124615-89-0Relevant academic research and scientific papers
Direct oxidation of secondary alcohol to ester by performic acid
Li, Xiao-Hong,Meng, Xiang-Guang,Liu, Ying,Peng, Xiao
, p. 3332 - 3336 (2013)
The reaction pathways and kinetics of the oxidation reactions of 1-phenylethyl alcohol (PEA), 1-(3,4-dimethoxyphenyl)ethanol (MVA), 1-(4-hydroxy-3-methoxyphenyl)ethanol (HMOPE), 1-(3-aminophenyl)ethanol (APE), 1-(4-methylphenyl)ethanol (MPE) and cyclohexanol with performic acid (PFA) were investigated in formic acid solvent. An unexpected new reaction pathway, from which the secondary alcohols can be directly oxidized to corresponding esters, was found. The reaction products (esters and ketones) of oxidation of PEA, MVA, HMOPE, APE, MPE and cyclohexanol were detected at different reaction times. The reaction rate constants, k1, k2, k3 and power orders α, β, γ of PFA concentration for three oxidation reactions pathways: alcohol to ester, alcohol to ketone and ketone to ester were obtained, respectively. These findings might provide a new insight into the technology of lignin degradation.
Making Carbonyls of Amides Nucleophilic and Hydroxyls of Alcohols Electrophilic Mediated by SO2F2 for Synthesis of Esters from Amides
Fang, Wan-Yin,Zha, Gao-Feng,Qin, Hua-Li
supporting information, p. 8657 - 8661 (2019/10/17)
We discovered that with the promotion of sulfuryl fluoride, the carbonyl groups of amides performed as nucleophiles while the hydroxyl groups of alcohols were activated to functionalize as electrophiles. This study displayed that the amide C-N bonds could be easily cleaved with delicate nucleophiles to form the ester C-O bonds at room temperature without using transition metals. The broad substrate scope and excellent functional group compatibility were proved with 44 examples in up to 99% yields.
Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols
Chapman, Robert S.L.,Francis, Molly,Lawrence, Ruth,Tibbetts, Joshua D.,Bull, Steven D.
, p. 6442 - 6452 (2018/10/02)
Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.
Purified mCPBA, a Useful Reagent for the Oxidation of Aldehydes
Horn, Alexander,Kazmaier, Uli
, p. 2531 - 2536 (2018/03/21)
Purified mCPBA is a useful reagent for the oxidation of several classes of aldehyde. Although linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α-branched ones undergo Baeyer–Villiger oxidation to formates. α-Branched α,β-unsaturated aldehydes provide enolformates and/or epoxides, which can be saponified to α-hydroxy ketones with shortening of the carbon chain by 1 carbon. Unbranched α,β-unsaturated aldehydes undergo an interesting Baeyer–Villiger oxidation/epoxidation/formate migration/BV oxidation cascade, which results in formyl-protected hydrates with an overall loss of two carbon atoms.
Lewis Base Promoted Reduction of CO2 with BH3NH3 into Boryl Formates: CO2 as a Carbon Source in Organic Synthesis Under Mild Conditions
Zhang, Bo,Du, Gaixia,Hang, Wei,Wang, Sheng,Xi, Chanjuan
supporting information, p. 1739 - 1743 (2018/04/24)
Lewis base promoted selective reduction of CO2 into boryl formates by using BH3NH3 as a reductant under mild conditions has been reported. The boryl formates, generated in situ, were shown to be reactive and versatile sources of formyl compounds to create new C–N, C–O, and C–C bonds. The reactivity of the boryl formates to yield formic acid, formamides, formates, secondary alcohols, and benzoheterocyclic rings was investigated.
Method for preparing formate-type compound
-
Paragraph 0039; 0047; 0048, (2018/07/30)
The invention discloses a method for preparing a formate-type compound. The method comprises the following steps of: adopting an alcohol-type compound and 1,3-dihydroxyacetone as reaction raw materials, and under the existence of a composite catalyst and an oxidant, reacting for 2-48 hours in a reaction medium in a reactor at a reaction temperature of 25-100 DEG C so as to obtain the formate-typecompound. The method disclosed by the invention is simple, and is mild in reaction condition, and by the method, a target product can be obtained by low cost and high yield; the used catalyst has highcatalytic activity, and is easily separated from a reaction system to be repeatedly used; the whole process is environment-friendly, and the reaction raw material (1,3-dihydroxyacetone) is easily converted from a side product (glycerol) of biodiesel, so that the utilization of the glycerol is promoted.
Homogeneous Palladium-Catalyzed Transfer Hydrogenolysis of Benzylic Alcohols Using Formic Acid as Reductant
Ciszek, Benjamin,Fleischer, Ivana
supporting information, p. 12259 - 12263 (2018/08/28)
We report the first homogeneous palladium-based transfer hydrogenolysis of benzylic alcohols using an in situ formed palladium-phosphine complex and formic acid as reducing agent. The reaction requires a catalyst loading as low as only 1 mol % of palladium and just a slight excess of reductant to obtain the deoxygenated alkylarenes in good to excellent yields. Besides demonstrating the broad applicability for primary, secondary and tertiary benzylic alcohols, a reaction intermediate could be identified. Additionally, it could be shown that partial oxidation of the applied phosphine ligand was beneficial for the course of the reaction, presumably by stabilizing the active catalyst. Reaction profiles and catalyst poisoning experiments were used to characterize the catalyst, the results of which indicate a homogeneous metal complex as the active species.
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
supporting information, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
MONOMER, POLYMER, RESIST COMPOSITION, AND PATTERNING PROCESS
-
, (2014/03/21)
A polymer comprising recurring units derived from a (meth)acrylate monomer of tertiary ester type having branched alkyl on alicycle is used to form a resist composition. When subjected to exposure, PEB and organic solvent development, the resist composition is improved in dissolution contrast.
Developing asymmetric iron and ruthenium-based cyclone complexes; Complex factors influence the asymmetric induction in the transfer hydrogenation of ketones
Hopewell, Jonathan P.,Martins, Jose E. D.,Johnson, Tarn C.,Godfrey, Jamie,Wills, Martin
experimental part, p. 134 - 145 (2012/01/12)
The preparation of a range of asymmetric iron and ruthenium-cyclone complexes, and their application to the asymmetric reduction of a ketone, are described. The enantioselectivity of ketone reduction is influenced by a single chiral centre in the catalyst, as well as by the planar chirality in the catalyst. This represents the first example of asymmetric ketone reduction using an iron cyclone catalyst.
