NaBH4/Ac2O/DOWEX(R)50WX4: A Convenient System for Fast Preparation of gem‐Diacetates from Aldehydes

Reductive‐acylalation of aldehydes has been carried out by NaBH₄/Ac₂O/DOWEX(R)50WX4 system. A variety of aldehydes (1 mmol) have been reacted with Ac₂O (0.5 mL) and NaBH₄ (1 mmol) in the presence of DOWEX(R)50WX4 (0.5 g) for the preparation of their corresponding acylals within 1 min at room temperature with excellent yields of the products (90‐95%). Ketones do not react with this system.     

Synthesis of Oximes with NH2OH.HCl/DOWEX(R)50WX4 System

The oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH₂OH·HCl system. The reactions were performed in ethanol to give Z‐aldoximation isomers of aldehydes and E‐oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.     

Water as a Green Solvent for Fast and Efficient Reduction of Carbonyl Compounds with NaBH4 under Microwave Irradiation

Reduction of varieties of carbonyl compounds such as aldehydes, ketones, α,β‐unsaturated aldehydes and ketones, α‐diketones and acyloins was carried out very fast and efficiently by sodium borohydride in water under microwave irradiation. The corresponding product alcohols were obtained in high to excellent yields.     

Fast and Efficient Reductive Amination of Aldehydes by NaBH4/B(OH)3 and NaBH4/Al(OH)3

Reductive amination a variety of aldehydes and anilines to their corresponding secondary amines were carried out with NaBH₄/B(OH)₃ and NaBH₄/Al(OH)₃ as new reducing systems in CH₃CN at room temperature in high to excellent yields of products (90‐96%).     

N-Methyl Piperidinium Chlorochromate Adsorbed on Alumina: A New and Selective Reagent for the Oxidation of Benzylic Alcohols to their Corresponding Carbonyl Compounds

Summary.  N-Methyl piperidinium chlorochromate adsorbed on alumina oxidizes a wide variety of benzylic alcohols to the corresponding carbonyl compounds. Received May 18, 2000. Accepted (revised) July 4, 2000     

Highly Efficient System for Reduction of Carboxylic Acids and Their Derivatives to Alcohols by HfCl4/KBH4

HfCl₄/KBH₄ was found to be a facile, efficient, convenient, and chemoselective system for the reduction of carboxylic acids and their derivatives to the corresponding alcohols under mild conditions. HfCl₄/NaBH₄ was also utilized to reduce the same carboxylic acids and their derivatives, and it was found that the reducing ability of HfCl₄/NaBH₄ was similar to that of HfCl₄/KBH₄. The action of HfCl₄/KBH₄ on other types of substrates, such as benzyl chloride, peracid, epoxide, ketone, amide, imine, pyridine-N-oxide, and nitrile, was investigated, too. In addition, some competitive reductions of styrene oxide in the presence of carboxylic acid, carboxylic ester, nitrile, and amide were achieved.     

Tetrakis (Pyridine)silver Dichromate Py4Ag2Cr207 - A Mild and Efficient Reagent for the Conversion of Benzylic and Allylic Alcohols to Their Corresponding Carbonyl Compounds

Tetrakis(pyridine)silver dichromate is prepared and used for the oxidation of benzylic and allylic alcohols in refluxing benzene in high yields.     

手性催化剂(4R)-苄氧基-(S)-脯氨酸的合成及其对不对称羟醛反应的催化活性

手性催化剂(4R)-苄氧基-(S)-脯氨酸的合成及其对不对称羟醛反应的催化活性;羟醛反应     

A Versatile Oxidizing Agent: Tetrakis-pyridino-cobalt(II) Dichromate Py4Co(HCrO4)2 (TPCD). Oxidations of Alcohols,Halides and Amines to Their Corresponding Carbonyl Compounds

The preparation of a versatile oxidizing agent tetrakis-pyridino-cobalt (II) dichromate Py₄Co(HCrO₄)₂ (TPCD) is presented and its structure is confirmed by x-ray crystal data. Alcohols, halides and amines are oxidized smoothly to their corresponding carbonyl compounds in good yields with TPCD.     

Reduction of Aromatic Nitro Compounds under Solvent‐Free Conditions Using Alumina‐Supported Hydrazine/FeNH4(SO4)2·12H2O

Aromatic nitro compounds were easily reduced to the corresponding amino compounds with hydrazine hydrate supported on alumina in the presence of FeNH₄(SO)₂·12H₂O.     

4-苄基氨甲酰苯基苯胺三氟甲磺酸盐(BCPPAT)：一种新型高效Friedel-Crafts苄基化和环己基化反应的催化剂

首次报道了一种新型高效、可循环使用的Friedel-Crafts反应催化剂——4-苄 基氨甲酰苯基苯胺三氟甲磺酸盐(BCPPAT)，它能够有效地催化芳烃的苄基化和环己 基化反应。     

Convenient and Efficient Method for the Iodination of Benzylic and Aliphatic Alcohols by Using Al(HSO4)3/KI in Nonaqueous Solution

A simple and efficient method for the iodination of benzylic and aliphatic alcohols by using Al(HSO₄)₃/KI in n‐hexane as solvent is reported. Mild reaction conditions and good to excellent yields of the products are the noteworthy advantages of the method.     

Efficient Reduction of Aryl Azides and Aryl Nitro Compounds to Their Corresponding Amines with Sulfurated Calcium Borohydride CA(BH2S3)2. A New Modified Borohydride Agent

Ca(BH₂S₃)₂ is easily prepared by metathetical reaction between NaBH₂S₃ and CaCl₂ in THF. Ca(BH₂S₃)₂ is much more stable than NaBH₂S₃ therefore, is a more practical reagent. Sulfurated calcium borohydride can easily reduce aryl nitro and aryl azido functions to their amines in high yields in refluxing THF. Reduction of nitro groups is accompanied with regioselectivity. Very high chemoselectivity is also observed for the reduction of an azido functional group in the presence of nitro functionality.     

Efficient Water Reduction with sp3‐sp3 Diboron(4) Compounds: Application to Hydrogenations,H–D Exchange Reactions,and Carbonyl Reductions

A series of crystalline sp³‐sp³ diboron(4) compounds were synthesized and shown to promote the facile reduction of water with dihydrogen formation. The application of these diborons as simple and effective dihydrogen and dideuterium sources was demonstrated by conducting a series of selective reductions of alkynes and alkenes, and hydrogen–deuterium exchange reactions using two‐chamber reactors. Finally, as the water reduction reaction generates an intermediate borohydride species, a range of aldehydes and ketones were reduced by using water as the hydride source.     

Antimony Trichloride: An Efficient and Mild Catalyst for Cyclization of 2-Aminochalcones to the Corresponding 2-Aryl-2,3-Dihydroquinolin-4(1H)-ones

Antimony trichloride is an efficient catalyst for the cyclization of 2-amino chalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones under mild reaction conditions and in almost quantitative yields.     

A chemoselective hydroxymethylation: new route for the synthesis of 6-aroyl-4-(4H-triazol-3-yl)thiomorpholin-3-ones

Treatment of 2-(2-oxo-2-arylethylthio)-N-(4H-1,2,4-triazol-3-yl)acetamides with paraformaldehyde in the presence of a base has led to a tandem chemoselective hydroxymethylation followed by cyclization yielding a set of novel 6-aroyl-4-(4H-triazol-3-yl)thiomorpholin-3-ones. The thiomorpholine ring has been found to have a boat like conformation in these compounds as evidenced by NOESY NMR spectrum.     

Facile and Efficient Synthesis of (R)‐4‐(Benzyloxy)‐3‐methylbutanenitrile: Toward Developing a Versatile Chiral Building Block

A practical synthesis of (R)‐4‐(benzyloxy)‐3‐methylbutanenitrile, a potential chiral building block, from the corresponding α‐keto ester in high yield and large scale was presented.     

Silica Sulfuric Acid and Al(HSO4)3: As Efficient Catalysts for the Formylation of Alcohols by Using Ethyl Formate under Heterogeneous Conditions

A mixture of ethyl formate and a catalytic amount of silica sulfuric acid or Al(HSO₄)₃ as suitable formylating systems can formylate various alcohols to their corresponding formate ester derivatives under mild, nearly neutral and heterogeneous conditions at room temperature with good to excellent yields.