71653-37-7

Upstream product

• 98-98-6 2-Picolinic acid 
• 500-32-3 N-benzyl-N,N-dimethyl-anilinium; dimethylphenylbenzylammonium hydroxide 
• 100-39-0 benzyl bromide 
• 25108-36-5 potassium picolinate 
• 105769-61-7 C₁₈H₁₃N₃O₂ 
• 100-51-6 benzyl alcohol 
• 109-09-1 2-chloropyridine 
• 201230-82-2 carbon monoxide 
• 100-70-9 2-Cyanopyridine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 1121-60-4 pyridine-2-carbaldehyde 
• 100-52-7 benzaldehyde 
• 108-88-3 toluene 

Downstream Products

• 100-51-6 benzyl alcohol 
• 14786-27-7 benzyl 4-nitrobenzoate 
• 18693-97-5 benzyl 4-cyanobenzoate 
• 1877-77-6 3-aminobenzenemethanol 

Relevant academic research and scientific papers

A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids

The Steglich esterification is a widely employed method for the formation of esters under mild conditions. A number of issues regarding the sustainability of this transformation have been identified, chiefly the use of hazardous carbodiimide coupling reagents in conjunction with solvents with considerable issues such as dichloromethane (DCM) and N,N-dimethylformamide (DMF). To overcome these issues, we have developed a solvent-reagent selection guide for the formation of esters via Steglich-type reactions with the aim of providing safer, more sustainable conditions. Optimum reaction conditions have been identified after high-throughput screening of solvent-reagent combinations, namely the use of Mukaiyama's reagent (Muk) in conjunction with solvent dimethyl carbonate (DMC). The new reaction conditions were also exemplified through the synthesis of a small selection of building-block like molecules and includes the formation of t-butyl esters.

A metal-free iodine-mediated conversion of hydroxamates to esters

A metal-, oxidant-, and additive-free conversion of hydroxamates to esters have been achieved using molecular iodine as the reagent using a novel but not-so-explored heron-type rearrangement. The reaction proceeds with almost equal facility with substrates having either electron-donating or electron-withdrawing substituent. Similarly, α,?-unsaturated, and sterically hindered ortho-substituted hydroxamates also undergo the desired transformation smoothly.

Picolinate-Directed Arene meta-C-H Amination via FeCl3 Catalysis

Direct C-H functionalization of aromatic compounds is a powerful tool for organic synthesis; however, differentiation among the ubiquitous and often chemically similar C-H bonds remains a significant challenge. Conflation with coordinating or directing groups incorporated into the intended substrate has helped address these limitations, although access to remote sites remains limited. Herein, we report an operationally simple and sustainable direct meta-selective H2N amination of benzylic and related aromatic picolinates under conditions mild enough to modify polyfunctional and late-stage molecules.

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br?nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

Thorium complexes possessing expanded ring N-heterocyclic iminato ligands: Synthesis and applications

Six and seven membered N-heterocyclic iminato ligands (L) are introduced allowing access a new class of Th(iv) complexes of the type Cp?2Th(L)(CH3). These complexes were studied in the Tishchenko reaction. Stoichiometric reactions together with kinetic and thermodynamic studies permit us to propose a plausible mechanism.

Esterification of the Primary Benzylic C-H Bonds with Carboxylic Acids Catalyzed by Ionic Iron(III) Complexes Containing an Imidazolinium Cation

The first iron-catalyzed esterification of the primary benzylic C-H bonds with carboxylic acids using di-tert-butyl peroxide as an oxidant is achieved by novel ionic iron(III) complexes containing an imidazolinium cation. The use of well-defined, air-stable, and available iron(III) complex in a 5 mol % loading and readily available starting materials with a broad generality and outstanding sterically hindered tolerance renders this methodology a useful alternative to other protocols that are typically employed for the synthesis of benzyl esters.

Synthesis of Esters by Functionalisation of CO2

The invention relates to a method for (I) producing a carboxylic ester of formula (I). Said method comprises the steps of: a) bringing an organosilane/borane of formula Si or B into contact with CO2, in the presence of a catalyst and an electrophilic compound of formula (III), the groups R1, R2, R3, R4, R5, Y, and M′ being as defined in claim 1; and optionally b) recovering the compound of formula (I) produced.

Nanocrystalline CeO2 as a Highly Active and Selective Catalyst for the Dehydration of Aldoximes to Nitriles and One-Pot Synthesis of Amides and Esters

The dehydration of aldoximes into nitriles has been performed in the presence of various metal oxides with different acid-base properties (Al2O3, TiO2, CeO2, MgO). The results showed that a nanocrystalline CeO2 was the most active catalyst. An in situ IR spectroscopy study supports a polar elimination mechanism in the dehydration of aldoxime on metal oxide catalysts, in which Lewis acid sites and basic sites are involved. The Lewis acid sites intervene in the adsorption of the oxime on the catalyst surface while surface base sites are responsible for the C1-H bond cleavage. Thus, the acid-base properties of nanocrystalline CeO2 are responsible for the high catalytic activity and selectivity. A variety of aldoximes including alkyl and cycloalkyl aldoximes have been dehydrated into the corresponding nitriles in good yields (80-97%) using nanosized ceria which moreover resulted in a stable and reusable catalyst. Additionally, it has been showed that a variety of pharmacologically important products such as picolinamide and picolinic acid alkyl ester derivatives can be obtained in good yields from 2-pyridinaldoxime in a one-pot process using the nanoceria as catalyst.

CO2 Conversion into Esters by Fluoride-Mediated Carboxylation of Organosilanes and Halide Derivatives

A one-step conversion of CO2 into heteroaromatic esters is presented under metal-free conditions. Using fluoride anions as promoters for the C-Si bond activation, pyridyl, furanyl, and thienyl organosilanes are successfully carboxylated with CO2 in the presence of an electrophile. The mechanism of this unprecedented reaction has been elucidated based on experimental and computational results, which show a unique catalytic influence of CO2 in the C-Si bond activation of pyridylsilanes. The methodology is applied to 18 different esters, and it has enabled the incorporation of CO2 into a polyester material for the first time. Metal free! A novel methodology is described to convert CO2 into heteroaromatic esters in the presence of organosilanes and organic halides using fluoride anions as promoters for the C-Si bond activation (see scheme). CO2 exhibits a unique catalytic influence in the C-Si bond cleavage of pyridylsilanes, serving as a traceless activator.

Selective Monoesterification of Symmetrical Diols Using Resin-Bound Triphenylphosphine

Coupling reactions to make esters and amides are among the most widely used organic transformations. We report efficient procedures for amide bond formation and for the monoesterification of symmetrical diols in excellent yields without any requirement for high dilution or slow addition using resin-bound triarylphosphonium iodide. Easy purification, low moisture sensitivity, and good to excellent yields of the products are the major advantages of this protocol.