A facile route to a polymer-supported IBX reagent

A three-step preparation of a polymer-supported IBX reagent from poly(p-methylstyrene) is reported. This reagent has been used successfully for the efficient oxidation of a series of alcohols to the corresponding aldehydes.     

Oxidation of threonine residues with IBX reagents

The treatment of protected Thr peptides with excess polymer-bound IBX effects sequential oxidation of the Thr secondary alcohol to the ketone, followed by hydroxylation of the alpha carbon of the Thr residues with loss of stereochemistry at this position.     

2-碘酰基苯甲酸(2-Iodoxybenzoic acid, IBX)在有机合成中的应用

综述了近年来2-碘酰基苯甲酸(2-iodoxybenzoic acid, IBX)在有机合成中的应用, 重点评述了IBX对醇类、含氮有机物、含硫有机物、连接在芳环上的碳原子的氧化反应, 探讨了IBX在α,β-不饱和羰基化合物和内酯合成中的应用, 这些反应具有反应条件温和、产率高、选择性好等优点. 简单介绍了IBX的一些新衍生物的合成及应用.     

A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residues with IBX

An efficient route to 3,4-dihydroxylphenylalanine (DOPA) and DOPA peptides was described by oxidation of l-tyrosine and l-tyrosine derivatives with 2-iodoxybenzoic acid (IBX). DOPA was obtained after an situ reduction of the corresponding ortho-quinone with sodium dithionite. Oxidation reactions proceeded in good yields and high chemo- and regio-selectivity. The chirality of the DOPA residue was retained under the reaction conditions. The efficiency and the selectivity of the reaction were successfully tested using recyclable polymer-supported IBX.     

Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 °C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described.     

Controllable and efficient oxidation of thioether by 2-iodoxybenzoic acid (IBX) in water: semisynthesis of sophocarpine

A metal-free, environment friendly, easy-to-operate, and efficient method for the semisynthesis of sophocarpine from matrine has been developed in an overall yield of 91%. The route features a controllable and efficient oxidation of thioether to sulfoxide by 2-iodoxybenzoic acid (IBX) in water.     

IBX/n-Bu4NBr/CH2Cl2-H2O: a new mild system for selective oxidation of secondary alcohols

A new alternative system for the chemoselective oxidation of secondary hydroxyl group to ketone with IBX/n-Bu₄NBr in CH₂Cl₂-H₂O has been developed. Under the reaction conditions, the secondary hydroxyl group was highly chemoselectively oxidized to the corresponding ketone, in moderate to good yields at rt, in the presence of primary hydroxyl group within the same molecule.     

A simple method for the oxidation of primary alcohols with o-iodoxybenzoic acid (IBX) in the presence of acetic acid

A simple method for the oxidation of primary alcohols to aldehydes using o-iodoxybenzoic acid (IBX) with the addition of stoichiometric acetic acid has been developed. Addition of acetic acid significantly accelerated the reaction rate. Under these conditions, primary aliphatic, benzylic, and allylic alcohols are smoothly converted to aldehydes in high yields (90-97%).     

The Influence of Ketones on the Formation of Symmetrical Secondary Amine: A New Method for Preparation of N, N-Bis-(dimethoxyphenylethyl)amine

InthecourseofhydrogenationofiminetoprepareDDPH,whichisanadrenoreceptorant.agonistandundergoesclinicstudyinChinanow',oneforeignmaterialN,N-Bis(dimethoxyphenylethyl)amineIwasformed(Schemel)'.IisanimportantintermediateforthepreparationofarrhythmicagentYS0353'4.Herewewouldliketoexplainitsformationandtheinfluenceofketoneonitsyield.Inschemel,whenweusedRaneyNiW,ascatalystunder40atm.H,pressure,40*nd5%Iwereobtained.Forimprovingtheyieldof2,weareattemptingtoreplaceRaneyNiW,bybasicRaneynickelto…     

2-碘酰基苯甲酸在有机合成中的研究与应用

高价有机碘化合物的反应性质与过渡金属相似,其参与的反应具有反应条件较温和、选择性好、产率高及环境友好等优点,因而近年来关于高价有机碘试剂的研究受到广泛关注,在有机合成领域中获得了较多应用.综述了近年来高价有机碘试剂2-碘酰基苯基酸(IBX)在有机合成中的研究及应用,包括IBX在氧化羟基、含氮化合物和含硫化合物,在制备α...     

Ferric(III) Nitrate Supported on Kieselguhr: A New Reagent for Selective Oxidation of Alcohols

A selective and effective oxidation of alcohols into the corresponding aldehydes and ketones, respectively, with a new reagent, ferric(III) nitrate supported on kieselguhr, under heterogeneous conditions is reported.     

Triphenylmethylphosphonium Dichromate: An Effective and Chemoselective Reagent for Oxidation of Benzylic Alcohols to the Corresponding Aldehydes and Ketones

An efficient and straightforward method for oxidation of the benzylic alcohols to the corresponding aldehydes and ketones has been accomplished using triphenylmethylphosphonium dichromate (MTPPD) under solvent-free conditions with high chemoselectivity. The reaction is fast with good yields and straightforward workup.     

Dimethyl Sulfoxide Pivaloyl Chloride: A New Reagent for Oxidation of Alcohols to Carbonyls

An efficient procedure for conversion of alcohols to the corresponding carbonyl compounds, an alternative to the classical Swern oxidation, is described. Pivaloyl chloride is employed as a mild and inexpensive electrophile. A possible reaction mechanism is proposed.     

Method for the Synthesis of 2-(2-Furyl)acrylonitriles

A new method was developed for the production of 2-(2-furyl)acrylonitriles on the basis of the Schmidt reaction.     

Selective Oxidation of Alcohols with a New Reagent: Iron(III) Nitrate Supported on Aluminum Silicate

A selective and effective oxidation of alcohols, except aliphatic alcohols, such as 1‐hexanol or 1‐octyl alcohol, to the corresponding aldehydes and ketones using a new reagent, iron(III) nitrate supported on aluminum silicate, under heterogeneous conditions with reflux with 85–98% yield is described.