Synthesis of New F-Alkyl β-Amino Alcohols

F-alkyl oxiranes 1 and p-methylbenzene sulfonate ester intermediates 3 derived from 2-F-alkyl ethane -1,2-diols 2 are converted into F-alkyl β-amino alcohols 5 respectively by a two-step process.     

Aqueous Media Oxidation of Alcohols with Ammonium Persulfate

Oxidation of series of various primary and secondary alcohols to corresponding carbonyl compounds with ammonium persulfate in aqueous media was described. No over oxidation of primary alcohols to carboxylic acids and secondary alcohols to esters was observed. Under such conditions benzoin was converted to benzoic acid.     

A Regio-and Stereoselective Synthesis of β-Amino Alcohols

The regio-and stereoselective ring opening of epoxide with aromatic amines catalyzed by samarium trichloride and the enantioselective ring opening of cyclohexene oxide with aniline catalyzed by lanthanide complexes were studied.     

Reactions of Polyfluorinated Telomeric Alcohols with ε-Caprolactam

The possibility of preparing fluorinated oligomeric derivatives of -aminocaproic acid by reaction of polyfluorinated telomeric alcohols H(CF₂CF₂) _n CH₂OH (n = 1-4) with -caprolactam under conditions of homogeneous catalysis (triethylamine, dimethylformamide) was examined. The thermal stability of the oligomers was studied in relation to the fluorine content.     

GaI_3 Catalyzed Tetrahydropyranylation of Alcohols and Phenols

Introduction Tetrahydropyranylation is an efficient method for the protection of hydroxyl group in organic synthesis due to the stability of the tetrahydropyranyl acetals because they are stable under a variety of reaction conditions such as alkaline media, Grignard reagents, lithium al-kyls, metal hydrides, oxidative reagents, alkylating and acylating reagents.1 Tetrahydropyranyl acetals are gen-erated by a nucleophilic addition of alcohols or phenols to 3,4-dihydro-2H-pyran (DHP). A variet…     

Gal3 Catalyzed Tetrahydropyranylation of Alcohols and Phenols

In dichloromethane, the nucleophilic addition of alcohols or phenols to 3,4-dihydro-2H-pyran (DHP) was catalyzed effectively by gallium triiodide which was generated in situ by the reaction of gallium metal and iodine to give the corresponding tetrahydropyranyl acetals in good to excellent yields.     

Triphenylphosphine-Catalyzed Michael Addition of Alcohols to Acrylic Compounds

A facile triphenylphosphine-catalyzed Michael addition of alcohols to acrylic compounds was described. The reaction was carried out in open air at refluxing temperature in the presence of 10 mol% PPh3. Michael addition of saturated and unsaturated alcohols to acrylonitrile or acrylates has been examined. The reaction gave β-alkoxy derivatives with isolated yields of 5%-79%. PPh3 is cheaper and more stable than those trialkylphosphines previously used for the similar reactions, and the products can be easily separated from the reaction mixture via distillation.     

Salen-Mn(III)-Complex-Catalyzed Oxidations of Secondary Alcohols

IntroductionCarbonylgroupsarethemostimportantfunctionalgroupsinorganicsynthesis ,andtheirintroductionbyoxi dationchemistrystartingfromalcoholsisaprocessofmajorimportance .1Earlyprotocolsforthistransformationreliedontheuseofstoichiometricoxidantssuchaschromium(VI)reagentsorMnO2 .2 Withthegoalofimprovingsyn theticefficiencyandavoidingpotentialenvironmentalhaz ards ,prominentsuccessinthisdirectionhasbeenrecentlyachievedbyutilizingmolecularoxygenwithanassistanceofpotenttransitionmetalcompounds.3…     

A Mild and Efficient Oxidation of Alcohols in Water

A mild and efficient oxidation of alcohols to the corresponding carbonyl compounds using the PhI(OAc)2 (1.1 eq.) with n-Bu4NBr (8 mol %) in water at room temperature is described.This new procedure is very simple and affords the desired carbonyl compounds in high yields.     

Microwave-assisted Oxidation of Alcohols and Polyarenes with Cetyltrimethylammonium Bromochromate

An efficient and mild methodology for oxidation of alcohols and polyarenes was described using cetyltrimethylammonium bromochromate (CTMABC) under microwave irradiation. Primary and secondary alcohols and polyarenes could be selectively oxidized under microwave irradiation into the corresponding aldehydes and ketones in high yields and short reaction time, using commercially available and magnetically retrievable oxidative material (CTMABC).     

CaY-zeolite Catalyzed Etherification and Alkylation of Substituted Benzyl Alcohols

Besides the great success in petroleum chemistry and related fields, the utilization of zeolites for selective organic synthesis has grown continuously in recent years1-3. The combination of acidic and shape selective properties of zeolites renders them p…     

Microwave‐Assisted NiCl2 Promoted Acylation of Alcohols

Abstract

A microwave oven acylation of alcohols by carboxylic acid anhydrides has been developed. NiCl₂ has been proven an efficient catalyst for the acylation of primary, secondary, and tertiary alcohols and phenols under microwave conditions.     

Formation of π-Allyl Palladium Complexes from Tertiary Alcohols

Reactions of 2-methyl-2-propanol, 2-methyl-2-butanol, 2-methyl-2-pentanol, 1-methyl-1-cyclohexanol, and 1-ethyl-1-cyclohexanol with palladium(II) tetraaqua complex in a perchloric acid medium give carbonyl and aromatic compounds, as well as the corresponding palladium -allyl complexes. The complexes were isolated from the reaction mixtures by way of formation of 2,2'-bipyridine complexes and characterized by the elemental analyses and ¹H and ¹³C NMR spectra. The main direction of transformation of acyclic alcohols is formation of complexes with no alkyl substituents at the central carbon atom of the allyl ligand; with cyclic alcohols, exocyclic complexes are formed.     

Salen-Mn（Ⅲ）-Complex-Catalyzed Oxidations of Secondary Alcohols

Secondary alcohols were catalytically oxidized with diace-toxyiodobenzene as oxidant in the presence of salen-Mn(Ⅲ)complex to aiTord the eorrespoltding ketones, in up to 99% yield, using CH2Cl2 or water as reaction media.     

A New Mathod for Conversion of Nitriles to Primary Alcohols

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Asymmetric Diethylzinc Addition to N-Diphenylphosphinoyl Benzalimine Mediated by Imino Alcohols

As our continuous efforts to search for easily accessible ligands for dialkylzinc addition to imines,[1] in this paper,we would like to present a family of chiral imino alcohols 3 derived from 1,2-diphenyl-2-aminoethanol which will be evaluated for the titled reaction. We believed that this kind of chiral ligands could be good chiral ligands for the diethylzinc addition to imines based on two points: (1) The excellent asymmetrically inductive properties of 1,2-diphenyl-2-aminoethanol and its derivatives have been proven in many reactions. (2) The conformation of the nitrogen in the chiral imines 3 is restricted by imine function which is similar to chiral oxazolines reported in our recent work.     

(E)-γ-Substituted Allylic Alcohols and α-Substituted Homoallylic Alcohols via Acidic Treatment of the Acetonides Derived from γ-Substituted Vinyl Diols

Treatment of the acetonides of γ-substituted vinyl diols under acidic deprotection conditions afforded γ-substituted allylic alcohols and α-substituted homoallylic alcohols.     

Phenylsulfonic Acid Functionalized Mesoporous Silica Catalyzed Transetherification of Alcohols with Dimethoxymethane

Phenylsulfonic acid functionalized mesoporous silica was synthesized by condensation of tetraethylorthosilicate with phenyltrimethoxysilane, and then sulfonation using 30% fuming sulfuric acid. The material was characterized using FT‐IR, DSC, XPS, TEM and N2 adsorption/desorption measurements. DSC revealed that sulfonic acid group of the catalyst was decomposed at 354.8°C, indicating that the catalyst exhibited high thermal stability. XPS showed that there existed three kinds of different silicon species on surface of the catalyst. The catalytic performance of the catalyst was evaluated using transetherification of alcohols with dimethoxymethane. It was found that among primary alcohols, the selectivities of the two long‐chain alcohols for n‐dedocanol and n‐tetradecyl alcohol were higher than 97.0% at the conversions of 43.6% and 65.3%, respectively, while the selectivities of the short‐chain alcohols except for n‐hexanol were less than 90.0% at the conversions of over 80.0%. Due to steric barrier, the secondary alcohols such as iso‐butanol and cyclohexanol afforded conversions of 79.4% and 60.5%, and the selectivities of the two alcohols were more than 90.0%. The sequence in conversion of the substituted phenols is as follows: p‐nitrophenol>p‐fluorophenol≥p‐bromophenol>p‐cresol>m‐cresol.     

Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by N-Sulfonylated Amino Alcohols

Asymmetric C-C bond forming reactions are of prime importance in modem synthetic organic chemistry. The use of chiral amino alcohol ligands is widespread in this area.[1] Herein, we describe the synthesis of N-sulfonylated amino alcohols 1～4 and enantioselective addition of diethylzinc to aldehydes was carried out employing titanium(Ⅳ) complexes 1～4.     

Catalytic Enantioselective Reduction of Prochiral Ketones with Chiral Ferrocenyl Amino Alcohols

The asymmetric reduction of prochiral ketones was catalyzed by a class of recoverable and highly stable chiral ferrocenyl amino alcohols derived from natural amino acids to yield optically active secondary alcohols in high chemical yields and moderate to good enantiomeric excesses.