5472-03-7

Upstream product

• 947700-72-3 C₂₇H₂₃NO 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 5720-05-8 4-methylphenylboronic acid 
• 94-41-7 benzalacetophenone 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 4224-87-7 4-methyl-chalcone 
• 3262-89-3 triphenylboroxine 
• 22252-14-8 (E)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one 
• 5084-80-0 tri(4-tolyl)boroxine 
• 1517-63-1 4-methylphenyl(phenyl)methanol 
• 614-20-0 3-oxo-3-phenylpropionic acid 

Downstream Products

• 129919-72-8 trans-2-(4-Methylphenyl)-1,1,3-triphenylcyclopropane 
• 129944-28-1 3-(4-Methylphenyl)-1,1,3-triphenylpropene 

Relevant academic research and scientific papers

Uncatalyzed conjugate addition of organozinc halides to enones in DME: A combined experimental/computational study on the role of the solvent and the reaction mechanism

Both aryl and alkylzinc halides prepared by direct insertion of zinc into organic halides in the presence of LiCl underwent the conjugate addition reaction to nonenolizable unsaturated ketones in excellent yield, provided that DME was used instead of THF as the solvent. Diffusion NMR measurements highlighted that the species undergo considerable aggregation under the experimental conditions used in the synthetic procedure, but no substantial differences have been found between the two solvents. Density functional theory calculations, prompted by the experimental aggregation study, revealed an unexpected reaction mechanism, where the coordinating capabilities of DME stabilize a transition state involving two organozinc moieties, lowering the activation energy of the reaction with respect to that seen for THF, enough to explain the fast and quantitative reactions observed experimentally and the different behaviors of the two solvents.

Heterogeneous catalytic 1,4-addition of arylmagnesium compounds to chalcones

Copper(II) on a 4 ? molecular sieve support catalyses the chemoselective addition of alkyl- and arylmagnesium halides to chalcones. Only the 1,4-addition products were obtained in high yields.

Stable and Reusable Palladium Nanoparticles-Catalyzed Conjugate Addition of Aryl Iodides to Enones: Route to Reductive Heck Products

An efficient, binaphthyl-backbone-stabilized palladium nanoparticles (Pd-BNP) catalyst for the 1,4-addition of aryl halides to enones has been developed. The scope of the reaction has been studied with various substituted and sterically hindered aryl hali

Synthesis, Coordination Properties, and Catalytic Application of Triarylmethane-Monophosphines

A new class of triarylmethane-based phosphines (L1-L4) and their Pd(II) and Rh(I) complexes were synthesized and subsequently characterized by NMR spectroscopy and X-ray diffraction analysis. The reactions of these phosphines with [PdCl(π-allyl)]2 gave the square-planar Pd(II) complexes [PdCl(π-allyl)(L)] (L = L1-L4). The treatment of [PdCl(π-allyl)(L3)] and [PdCl(π-allyl)(L4)], which have CF3-substituted triarylmethane and 9-arylfluorene moieties, respectively, with LiOtBu afforded P,C(sp3)-chelated palladacycle complexes. Reversibility between a C(sp3)-M covalent bond and a C(sp3)-H···M interaction was experimentally demonstrated using [RhCl(nbd)]2 as a Rh(I) source. The triarylmethane-monophosphines L1-L4 were applied to the Pd-catalyzed 1,4-addition of arylboronic acids to enones.

Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

Ligand-free nickel-catalysed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds

A simple and efficient ligand-free nickel-based catalytic system has been developed for the 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds. With catalyst loadings of 1-2 mol%, a series of 1,4-adducts from chalcones and cinnamates was obtained in moderate to excellent yields within 5-30 min under a nitrogen atmosphere and microwave irradiation. The 1,4-addition of arylboronic acids to acrylates is less efficient.

Decarboxylative substitution of β-keto acids to benzylic alcohols catalyzed by molecular iodine

An efficient method for molecular iodine catalyzed decarboxylative substitution of β-keto acids with benzylic alcohols under mild conditions has been described and valuable α-functionalized ketones were obtained in good to excellent yields.

Tandem aldol condensation/platinacycle-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids

Aldol condensation of aldehydes with methyl ketones followed by anionic four-electron donor-based (type I) platinacycle-catalyzed addition reactions of arylboronic acids to form β-arylated ketones is described. Good to excellent yields of β-arylated ketones were obtained for the tandem reactions of aromatic/aliphatic aldehydes, methyl ketones, and arylboronic acids, and moderate yields were observed for the tandem reactions of α,β-unsaturated aldehydes. The aldol condensation of aldehydes with methyl ketones was successfully combined with the platinacycle-catalyzed addition reactions of arylboronic acids in a tandem fashion. A variety of β-arylated ketones was obtained in good to excellent yields.

Palladium-catalyzed desulfitative addition of sodium sulfinates with α,β-unsaturated carbonyl compounds

A palladium-catalyzed desulfitative conjugate addition of sodium sulfinates with α,β-unsaturated carbonyl compounds is described. The reaction showed very good selectivity and tolerated a wide range of functionalities under an atmosphere of argon.

Sequential aldol Condensation-Transition metal-Catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids

Sequential aldol condensation of aldehydes with methyl ketones followed by transition metal-catalyzed addition reactions of arylboronic acids to form β-substituted ketones is described. By using the 1,1′;-spirobiindane- 7,7′;-diol (SPINOL)-based phosphite, an asymmetric version of this type of sequential reaction, with up to 92% ee, was also realized. Our study provided an efficient method to access β-substituted ketones and might lead to the development of other sequential/tandem reactions with transition metal-catalyzed addition reactions as the key step.