10522-23-3

Upstream product

• 201230-82-2 carbon monoxide 
• 827-54-3 2-naphthylethylene 
• 38964-52-2 (±)-2-(naphthalen-2-yl)propan-1-ol 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 581-96-4 2-naphthylacetic acid 
• 2876-71-3 methyl 2-naphthylacetate 
• 57421-64-4 methyl α-(2-naphthyl)propionate 
• 873932-84-4 2-(naphthalen-2-yl)prop-2-en-1-ol 
• 21567-68-0 1-(naphthalen-2-yl)propan-2-one 
• 854248-80-9 1-(1-methoxyprop-1-en-2-yl)naphthalene 
• 3710-23-4 2-isopropenylnaphthalene 
• 93-08-3 methyl 2-naphthyl ketone 
• 600697-54-9 ethyl 3-methyl-3-(2-naphthyl)oxirane-2-carboxylate 
• 256229-37-5 methyl enol ether of 2-(naphthalen-2-yl)propanal 

Downstream Products

• 1342313-23-8 2-methyl-2-(naphthalen-2-yl)-4-(1-phenyl-1H-tetrazol-5-ylsulfonyl)butanal 
• 93-08-3 methyl 2-naphthyl ketone 

Relevant academic research and scientific papers

Substituent effects in the rhodium catalyzed hydroformylation of olefins using bis(diarylphosphino)methylamino ligands

Rhodium-complexes of bis(diarylphosphino)methylamino ligands RN(CH2PPh2)2 are active catalysts in the hydroformylation of 1-octene and 2-vinylnaphthalene, regioselectivity (n/iso-ratio) and catalyst activity (TOF) depending upon the nature of the para-substituent in the N-aryl moiety (R = C6H5, p-CF3-C6H4, P-NMe2-C6H4).

Solvent-free olefin hydroformylation using hemispherical diphosphites

With rhodium complexes containing hemispherical diphosphite ligands derived from a calixarene skeleton, olefins can be hydroformylated efficiently under solvent-free conditions. For example, in the hydroformylation of 1-octene (T = 80 °C, P = 20 bar, olefin:Rh = 200 000:1) one of the catalysts investigated resulted in a TOP of 17290 mol (converted 1-octene)mol(Rh)-1h -1, the regioselectivity towards the linear aldehyde reaching then 97.9%.

Carbon dioxide gas accelerates solventless synthesis

Some solventless reactions involving solid reactants or products can be accelerated by the influence of subcritical gaseous CO2.

Pyrazoles as ligands for the Rh-catalyzed hydroformylation of alkenes in supercritical carbon dioxide

Activity of pyrazole ligands in hydroformylation of a number of unsaturated terminal substrates in supercritical carbon dioxide (scCO2) in the presence of Rh-catalyst was studied. The ligands without free NH group at position 1 of the pyrazole ring were found to be active. The use of scCO 2 as the reaction medium served to reach a higher conversion and regioselectivity of hydroformylation as compared to those in toluene.

Regioselective hydroformylation of vinylarenes in aqueous media by a sol-gel entrapped rhodium catalyst

Two methods for selective hydroformylation of vinylarenes in aqueous media are described. One method relies on the application of [Rh(cod)Cl]2 and a tertiary phosphane entrapped within an ionic liquid-confined silica sol-gel support. The second method utilizes the same rhodium compound, encaged within ionic-liquid-free hydrophobicized sol-gel. Both methods are best carried out at 50 °C in aqueous emulsions or microemulsions that consist of the substrate, a surfactant, a co-surfactant and >89% water. The optimal H 2/CO ratio is between 1 and 1.1. Both methods allow the reuse of the heterogenized catalyst for several runs. While the regioselectivity and the yield are hardly affected by the electronic nature of the substrates, they are significantly dependent on the reaction temperature, on the surfactant employed, and on the hydrophobicity of the support of the catalyst. Despite the use of H2 in the reactions, no transformation of the organometallic catalyst into metallic nanoparticles could be detected.

Enantioselective Synthesis of (?)-Halenaquinone

The efficient, 12–14 step (LLS) total synthesis of (?)-halenaquinone has been achieved. Key steps in the synthetic sequence include: (a) proline sulfonamide-catalyzed, Yamada–Otani reaction to establish the C6 all-carbon quaternary stereocenter, (b) multi

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.

syn-Selective Michael Reaction of α-Branched Aryl Acetaldehydes with Nitroolefins Promoted by Squaric Amino Acid Derived Bifunctional Br?nsted Bases

Here we describe a direct access to 2,2,3-trisubstituted syn γ-nitroaldehydes by addition of α-branched aryl acetaldehydes to nitroolefins promoted by a cinchona based squaric acid-derived amino acid peptide. Different α-methyl arylacetaldehydes react with β-aromatic and β-alkyl nitroolefins to afford the Michael adducts in high enantioselectivity and syn-selectivity. NMR experiments and DFT calculations predict the reaction to occur through the intermediacy of E-enolate. The interaction between the substrates and the catalyst follows Pápai's model, wherein an intramolecular H-bond interaction in the catalyst between the NH group of one of the tert-leucines and the squaramide oxygen seems to be key for discrimination of the corresponding reaction transition states.

Copper-catalyzed hydroformylation and hydroxymethylation of styrenes

Hydroformylation catalyzed by transition metals is one of the most important homogeneously catalyzed reactions in industrial organic chemistry. Millions of tons of aldehydes and related chemicals are produced by this transformation annually. However, most of the applied procedures use rhodium catalysts. In the procedure described here, a copper-catalyzed hydroformylation of alkenes has been realized. Remarkably, by using a different copper precursor, the aldehydes obtained can be further hydrogenated to give the corresponding alcohols under the same conditions, formally named as hydroxymethylation of alkenes. Under pressure of syngas, various aldehydes and alcohols can be produced from alkenes with copper as the only catalyst, in excellent regioselectivity. Additionally, an all-carbon quaternary center containing ethers and formates can be synthesized as well with the addition of unactivated alkyl halides. A possible reaction pathway is proposed based on our results. This journal is

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.