3888-64-0

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 71-36-3 butan-1-ol 
• 1195931-62-4 butyl 4-(((trifluoromethyl)sulfonyl)oxy)benzoate 
• 201230-82-2 carbon monoxide 
• 225916-39-2 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 57728-63-9 4-fluoro-N-(2-hydroxyethyl)-benzamide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 1283075-99-9 dipropan-2-yl 1-(4-fluorobenzoyl)hydrazine-1,2-dicarboxylate 
• 459-22-3 4-fluorophenylacetonitrile 
• 109-65-9 1-bromo-butane 
• 459-56-3 4-fluorobenzylic alcohol 
• 456-22-4 4-Fluorobenzoic acid 
• 109-69-3 n-Butyl chloride 

Relevant academic research and scientific papers

Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source

Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]

Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones

The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.

Nickel-Catalyzed Esterification of Amides Under Mild Conditions

Abstract: The use of ligands to adjust the catalytic activity of the catalyst for esterification of amides is challenge in organic chemistry. In this paper, Nickel(II)-NHC-catalyzed the esterification reaction between N,N-di-Boc amide and alcohols at room temperature have been demonstrated. The imidazolium salt bearing a hydroxyl functionalized side arm showed high effective catalytic activity in the activation of the amide N–C bond in air atmosphere. Graphic Abstract: [Figure not available: see fulltext.].

A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions

The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.

Dehydrogenative cross-coupling of primary alcohols to form cross-esters catalyzed by a manganese pincer complex

Base-metal-catalyzed dehydrogenative cross-coupling of primary alcohols to form cross-esters as major products, liberating hydrogen gas, is reported. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of catalytic base, without any hydrogen acceptor or oxidant. Mechanistic insight indicates that a dearomatized complex is the actual catalyst, and indeed this independently prepared dearomatized complex catalyzes the reaction under neutral conditions.

Electrochemical C(sp 3)-H Fluorination

A simple and robust method for electrochemical alkyl C-H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C-H bonds are converted into their C-F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.

Palladium-Catalyzed Alkoxycarbonylation of Arylsulfoniums

Alkoxycarbonylation of arylsulfoniums has been developed with the aid of a catalytic amount of a palladium-Xantphos complex under an atmospheric pressure of CO gas. Various functional groups such as carbonyl, cyano, halo, and sulfonyl groups were well tolerated under the present catalysis. Since aryldimethylsulfoniums were readily prepared from the corresponding aryl methyl sulfides and methyl triflate, one-pot alkoxycarbonylation of aryl methyl sulfides could be accomplished.

Synthetic method of an ester compound

The invention discloses a synthetic method of an ester compound and belongs to the technical field of organic synthesis. The synthetic method includes the steps of: dissolving an aldehyde compound (1) and a halogenated hydrocarbon compound (2) in a solvent, adding an oxidant and a catalyst, and performing a reaction at 60-100 DEG C to obtain the target product ester compound (3). A reaction equation of the synthetic method is represented as follows. The method, compared with the prior art, has the following advantages: 1) the raw materials are easy to obtain and are low in cost; 2) the reaction conditions are mild, operations are simple, and reaction time is short; and 3) a substrate has wide available range and can be used for synthesis of various ester compounds.

Fe-Catalyzed Aerobic Oxidative C-CN Bond Cleavage of Arylacetonitriles Leading to Various Esters

Fe-catalyzed aerobic oxidative esterifications of arylacetonitriles with alcohols, tri alkoxsilanes, silicate esters, or borate esters have been developed. The acyl groups which were in situ generated via chemoselective C(CO)-CN bond cleavage were directly used as electrophiles, leading to corresponding aryl esters in good to excellent yields under molecular oxygen when attacked by alcohols or alcohol surrogates. Dioxygen serves as both oxidant and reactant in this protocol. The reaction has a very broad substrate scope. Cheap starting materials as well as environmentally benign and inexpensive iron catalyst and ideal oxidant O2 feature this transformation and make it a practical and sustainable protocol to afford esters.

A facile, one-pot procedure for the conversion of aromatic aldehydes to esters, as well as thioesters and amides, via acyl hydrazide intermediates

Herein we present an efficient method for the synthesis of esters from aromatic aldehydes via readily accessible acyl hydrazides. The developed reaction protocol is shown to be tolerant of a range of aromatic aldehydes, bearing various functionalities, as well as being amenable to the synthesis of thioesters and amides.