38612-11-2

Upstream product

• 459-56-3 4-fluorobenzylic alcohol 
• 101-41-7 benzeneacetic acid methyl ester 
• 352-32-9 p-fluorotoluene 
• 65-85-0 benzoic acid 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 98-88-4 benzoyl chloride 
• 30148-17-5 (1-methyl-1H-imidazol-2-yl)(phenyl)methanone 
• 99802-96-7 2-benzoyl-1,3-dimethyl-1H-imidazol-3-ium iodide 
• 3831-29-6 4-fluorobenzyl iodide 
• 18819-89-1 tetrabutylammonium benzoate 
• 55-21-0 benzamide 
• 120-46-7 1,3-diphenylpropanedione 
• 100-51-6 benzyl alcohol 

Relevant academic research and scientific papers

Transition metal free oxidative esterification of alcohols with toluene

Using Bu4NI as the catalyst and tert-butyl hydroperoxide as the oxidant, direct esterification of alcohols with toluene derivatives was achieved. Mechanistic investigations indicate that the alcohols are sequentially oxidized to aldehydes, carboxylic acids, and then to benzyl esters. Bu 4N+ functions as a phasetransfer reagent and iodide catalyzes the reaction.

Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters

The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]

Base-Promoted Amidation and Esterification of Imidazolium Salts via Acyl C-C bond Cleavage: Access to Aromatic Amides and Esters

Imidazolium salts have been effectively employed as suitable acyl transfer agents in amidation and esterification in organic synthesis. The weak acyl C(O)-C imidazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcohols to afford amides and esters. The broad substrate scope of anilines and benzylic amines and base-promoted conditions are the benefits of this route. Interestingly, phenol, benzylic alcohols, and a biologically active alcohol can also be subjected to esterification under the optimized conditions.

Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp3-H bond activation under metal-free conditions

A metal-free protocol for the direct oxidative esterification of the Csp3-H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.

Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical

Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy.

Versatile and sustainable alcoholysis of amides by a reusable CeO 2 catalyst

CeO2 catalyzed the esterification between an equivalent molar ratio of primary amides and alcohols under neutral conditions, which provides the first versatile reusable catalytic system for direct alcoholysis of amides to esters with wider scope and 67 times higher turnover number (TON) than previous catalytic systems.

Cu-catalyzed esterification reaction via aerobic oxygenation and C-C bond cleavage: An approach to α-ketoesters

The Cu-catalyzed novel aerobic oxidative esterification reaction of 1,3-diones for the synthesis of α-ketoesters has been developed. This method combines C-C σ-bond cleavage, dioxygen activation and oxidative C-H bond functionalization, as well as provides a practical, neutral, and mild synthetic approach to α-ketoesters which are important units in many biologically active compounds and useful precursors in a variety of functional group transformations. A plausible radical process is proposed on the basis of mechanistic studies.

CeO2 as a versatile and reusable catalyst for transesterification of esters with alcohols under solvent-free conditions

CeO2 acted as an efficient and reusable heterogeneous catalyst for transesterification of esters with alcohols under the solvent-free conditions at 160 °C. Among the 11 kinds of metal oxides, CeO2 is the most suitable catalyst in terms of catalytic activity, leaching-resistance and reusability. This catalytic system tolerates various esters and alcohols, and valuable esters such as heteroaromatic esters and benzyl benzoates are produced, demonstrating a practical utility of the system. On the basis of kinetic analysis and in situ IR studies of adsorbed species, a reaction mechanism is proposed, in which proton abstraction of alcohol by a Lewis base site of CeO2 to yield alkoxide species is the rate-limiting step.