30611-16-6

Upstream product

• 100-13-0 4-nitrostyrene 
• 201230-82-2 carbon monoxide 
• 105-39-5 chloroacetic acid ethyl ester 
• 100-19-6 (4-nitrophenyl)ethanone 
• 75590-19-1 p-nitro-α-methylstyrene oxide 
• 109942-40-7 sodium 3-methyl-3-(4-nitrophenyl)oxirane-2-carboxylate 
• 100193-16-6 ethyl 3-methyl-3-(4-nitrophenyl)oxirane-2-carboxylate 
• 64-17-5 ethanol 
• 107-18-6 allyl alcohol 
• 76346-07-1 (E)-4,4'-(but-1-ene-1,3-diyl)bis(nitrobenzene) 

Downstream Products

• 63489-72-5 2-(4-Nitrophenyl)-1-propanol 
• 100-19-6 (4-nitrophenyl)ethanone 
• 1440418-53-0 (R)-di-tert-butyl 1-(2-(4-nitrophenyl)-1-oxo-propan-2-yl)hydrazine-1,2-dicarboxylate 

Relevant academic research and scientific papers

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds

A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.

Copper-catalyzed vinylogous aerobic oxidation of unsaturated compounds with air

A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.

Surface bonded Rh-bis(diarylphosphine) on magnetic nanoparticles as a recyclable catalyst for hydroformylation of olefins

A functionalized nanomaterial having an average particles size of less than 10 nm comprising an iron oxide nanoparticle core and a bis(diarylphosphinomethyl) dopamine based ligand layer anchored to the iron oxide nanoparticle core is disclosed. In addition, a catalyst composition for use in a variety of chemical transformations wherein the bisphosphine groups of the functionalized nanomaterial chelate a catalytic metal is disclosed. In addition, a method for producing the functionalized nanomaterial and a method for the hydroformylation of olefins to aldehydes employing the functionalized nanomaterial with high conversion percentage and high selectivity are disclosed.

Dual Catalysis Using Boronic Acid and Chiral Amine: Acyclic Quaternary Carbons via Enantioselective Alkylation of Branched Aldehydes with Allylic Alcohols

A ferrocenium boronic acid salt activates allylic alcohols to generate transient carbocations that react with in situ-generated chiral enamines from branched aldehydes. The optimized conditions afford the desired acyclic products embedding a methyl-aryl quaternary carbon center with up to 90% yield and 97:3 enantiomeric ratio, with only water as the byproduct. This noble-metal-free method complements alternative methods that are incompatible with carbon-halogen bonds and other sensitive functional groups.

A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes

A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.

β-tert-Butyl aspartate as an organocatalyst for the asymmetric α-amination of α,α-disubstituted aldehydes

The enantioselective α-amination reaction of α,α- disubstituted aldehydes can lead to a variety of enantioenriched amino aldehydes, amino alcohols, and amino acids. After screening a variety of amino acids and their derivatives, we identified a cheap, simple, commercially available aspartic acid derivative that can catalyze efficiently the reaction between α,α-disubstituted aldehydes and dialkyl azodicarboxylates. The reaction proceeds smoothly leading to the corresponding α-aminated adducts in moderate to quantitative yields and moderate to high enantioselectivities (up to 96% ee). Finally, the conversion of these adducts to α,α-disubstituted quaternary amino acids is also described.

Oxidative cleavage of α-aryl aldehydes using iodosylbenzene

We found that α-aryl aldehydes can be cleaved to chain-shortened carbonyl compounds and formaldehyde by various iodosylbenzene complexes. A mechanistic scheme is presented that accounts for the loss of one carbon atom. Formaldehyde is further oxidized to CO and CO2 under the reaction conditions.

Effective construction of quaternary stereocenters by highly enantioselective α-amination of branched aldehydes

A highly efficient enantioselective α-amination of branched aldehydes with azadicarboxylates promoted by chiral proline-derived amide thiourea bifunctional catalysts was developed for the first time, affording the adducts bearing quaternary stereogenic centers with excellent yields (up to 99%) and enantioselectivities (up to 97% ee).

The proline-catalyzed asymmetric amination of branched aldehydes

An efficient access to configurationally stable α,β- disubstituted α-amino aldehydes, oxazolidinones, and α-amino acids has been presented. Starting from simple and easily available racemic aldehydes, the α-aminated products were obtained using azodicarboxylates as the nitrogen source in up to 86 % ee and moderate to excellent yield. These products could further be converted both into the corresponding α-amino alcohols and, depending on the residue of the azodicarboxylates and the reaction conditions, into the oxazolidinones. On the other hand, oxidation towards the carboxylic acid and cleavage of the hydrazide bond under mild conditions revealed the free α-alkylated phenylglycine derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.