52468-48-1

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 71-36-3 butan-1-ol 
• 201230-82-2 carbon monoxide 
• 615-41-8 2-iodochlorobenzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 609-66-5 2-chlorobenzamide 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 694-80-4 2-bromo-1-chlorobenzene 
• 37170-50-6 di(methyl)tert-butyl(n-butoxy)silane 
• 89-98-5 2-chloro-benzaldehyde 
• 58274-24-1 1-Chloro-2-dibutoxymethyl-benzene 

Downstream Products

• 17261-28-8 ortho-diphenylphosphinobenzoic acid 

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.]

Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations

The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcohols, and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki–Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.

Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas

A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.

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.

Fe3O4 supported Pd(0) nanoparticles catalyzed alkoxycarbonylation of aryl halides

This paper describes the simple and efficient method for the alkoxycarbonylation of aryl iodides using magnetically recoverable Pd/Fe 3O4 as the catalyst under atmospheric pressure of carbon monoxide. Various aryl iodides on alkoxycarbonylation with alcohols gave the corresponding products in good to excellent yields. The catalyst is completely recoverable with the simple application of an external magnetic field, and the efficiency of the catalyst remains unaltered even after five cycles.

Combined catalytic system of scandium triflate and boronic ester for amide bond cleavage

We have found that the combination of scandium with boronic ester enables the cleavage of amide bonds. Primary amides were converted to the corresponding esters in the presence of catalytic amounts of scandium triflate and boronic ester under mild and neutral conditions. This unique catalytic system can be applied to the deprotection of acetylaniline derivatives. In addition, control NMR experiments were carried out to examine the effect of the boronic esters. Copyright

Iron(III) chloride-promoted direct conversion of aryl/alkyl cyanides to esters

Aryl/alkyl cyanides were quickly converted into the corresponding esters in the presence of iron(III) chloride in refluxing alcohols with very good yields. Copyright Taylor & Francis Group, LLC.

Catalytic processes of oxidation by hydrogen peroxide in the presence of Br2 or HBr. Mechanism and synthetic applications

The mechanism and the synthetic applications for the oxidation of alcohols, ethers, and aldehydes by H2O2 catalyzed by Bf2 or Br- in a liquid two-phase system (aqueous and organic) are reported. Aliphatic and benzylic primary alcohols and ethers show an opposite behavior, which has been rationalized on the ground of the different electronic configurations of the intermediate alkyl (π-type) and acyl (σ-type) radicals and their influence on enthalpic and polar effects. A two-phase system is particularly useful also for an efficient benzylic bromination by Br2 or Br-; the substitution of the benzyl bromide by OH, OR, and OCOR regenerates Br-, which can be recycled. The evaluation of the relative reactivities of the involved substrates and intermediates has allowed to develop a variety of simple, facile, convenient, and selective syntheses of alcohols, aldehydes, ketones, esters, and benzyl bromides, which fulfill the conditions for practical applications.

Substituents Effect on the Reaction of Aromatic Acetals Over Aluminium Phosphate and Aluminium Sulphate Catalyst

Aromatic acetals in the presence of aluminium phosphate (AP) catalyst at elevated temperatures yield the corresponding esters (b), ethers (c) and the parent aldehydes (d).These substrates over aluminium sulphate (AS) catalyst give only the esters (b) and aldehydes (d).The products distribution varies with temperature.Substituents in the ring also play a part in the reaction.

REARRANGEMENT OF SUBSTITUTED AROMATIC ACETALS CATALYSED BY γ-ALUMINA

Aromatic acetals over γ-alumina undergo rearrangement to give the corresponding esters (b) and ethers (c) in good yield.The product distribution varied unusually over the range of reaction temperatures.The effect of substituents has also been felt much in the study.Probable mechanisms have been suggested for the reaction.The catalyst has been characterized by various studies and the specific poisoning of the catalyst has been done with NH3, CO2 and H2S.