74395-08-7

Upstream product

• 100396-69-8 3-phenyl-cyclohepta-2,4-dienone 
• 1121-66-0 2-Cyclohepten-1-one 
• 62-53-3 aniline 
• 98-80-6 phenylboronic acid 
• 780-69-8 triethoxyphenylsilane 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 615-53-2 ethyl N-methyl-N-nitrosocarbamate 
• 591-51-5 phenyllithium 
• 52205-01-3 (5-methyl-2-phenyl-[1,3,2]dioxaborinan-5-yl)-methanol 
• 1352708-09-8 trimethyl((5-methyl-2-phenyl-1,3,2-dioxaborinan-5-yl)methoxy)silane 
• 143-66-8 sodium tetraphenyl borate 
• 94683-33-7 3-phenyl-5-(toluene-4-sulfonyloxymethyl)-cyclohex-2-enone 
• 91909-41-0 5-hydroxymethyl-3-phenyl-cyclohex-2-enone 

Downstream Products

• 1190306-02-5 methyl 2-oxo-4-phenylcycloheptanecarboxylate 
• 19217-54-0 3-phenylcycloheptene 
• 100650-88-2 4-phenylcycloheptene 
• 19217-56-2 3-Phenyl-cycloheptanol 

Relevant academic research and scientific papers

The synthesis method of one-carbon ring expansion of cycloketone dericatives from β-selenyl cycloketone dericatives

The present invention relates to a method for preparing a cyclic ketone derivative with an increased carbon number by performing a ring expansion reaction of a β-selenyl cyclic ketone derivative. The present invention was first developed by performing the

4,8-disubstituted bicyclo[3.3.1]nona-2,6-dienes as chiral ligands for rh-catalyzed asymmetric 1,4-addition reactions

C2-symmetric chiral diene ligands based on 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene framework have been designed and synthesized. The rhodium complexes of the dienes, which were obtained in a few straightforward steps from enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione, exhibited excellent catalytic activity and high enantioselectivity (up to 96% ee) in the conjugate addition reaction of arylboronic acids to cyclic enones under mild reaction conditions with high atom efficiency. Chiral C2-symmetric 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene ligands were synthesized from easily available bicyclo[3.3.1]nonane-2,6-dione and utilized in the asymmetric 1,4-addition reaction of arylboronic acids to cyclic enones. The catalyst prepared in situ from ligand 4b and [RhCl(C2H4)2]2 exhibited excellent catalytic activity and high enantioselectivity (up to 96% ee) under mild reaction conditions with high atom efficiency.

1,4-Addition of aryl boronic acids to α,β-unsaturated ketones catalyzed by a CCC-NHC pincer rhodium complex

An air- and water-stable CCC-NHC pincer Rh complex catalyzed the 1,4-addition of aryl boronic acids to α,β-unsaturated ketones and aldehydes. This bench top method proceeds in eco-friendly solvents including methanol and water. The scope of boronic acids was expanded to include heterocyclic examples.

New methylene homologation method for cyclic ketones

Teaching new tricks to an old dog: By intercepting adducts between ketones and lithium trimethylsilyldiazomethane, a new Tiffeneau-Demjanov type methylene homologation could be realized in a single-step operation. Among proton sources and Lewis acids, silica gel was found to be the most effective reagent for the protonation of intermediates and their subsequent ring expansion (see scheme). Copyright

Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds

A novel rhodium-catalyzed conjugate addition of indium reagents to electron deficient olefins is reported. The reaction takes place in THF/MeOH at 110 °C using arylindium dichlorides, a rhodium(I)-binap complex as catalyst, and α,β-unsaturated ketones and

Rhodium-catalysed enantioselective synthesis of 4-arylchroman-2-ones

The rhodium-catalysed enantioselective 1,4-addition of organoboron reagents to arylidene Meldrum's acids as acceptors, allows convenient access to 4-arylchroman-2-ones with good to excellent levels of enantioselectivity. The use of silyl-protected dioxabo

Preparation, hydrogen bonds, and catalytic activity in metal-promoted addition of arylboronic acids to enones of a rhodium complex containing an NHC ligand with an alcohol function

The complex RhCl(COD){3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazol-2- ylidene} has been prepared by reaction of the dimer [Rh(μ-OMe)(COD)] 2 with 3-benzyl-1-(2-hydroxy-2-phenylethyl)imidazolium chloride and characterized by X-ray diffraction analysis. The structure reveals that 75% of the molecules are associated through intermolecular O-H...Cl hydrogen bonds between the OH group of the NHC substituent of one molecule and the chloride ligand of the adjacent molecule. This complex catalyzes the addition of arylboronic acids to cyclic and acyclic enones in anhydrous toluene. The alcohol function of the substituent of the NHC ligand plays the role assigned to water in previous cases.

Molecular-architecture-based administration of catalysis in water: Self-assembly of an amphiphilic palladium pincer complex

Testing the waters: An architecture-based system for transition-metal catalysis consisting of a self-assembled amphiphilic pincer palladium complex bearing hydrophilic and hydrophobic chains has been developed. Self-assembly of the bilayer vesicles of the complex, concentration of the organic substrates within the hydrophobic region of the bilayer membrane, and catalytic transformation of the substrate all occur sequentially in water (see scheme). Copyright

A homogeneous, recyclable polymer support for rh(I)-catalyzed c-c bond formation

A robust and practical polymer-supported, homogeneous, recyclable biphephos rhodium(I) catalyst has been developed for C-C bond formation reactions. Control of polymer molecular weight allowed tuning of the polymer solubility such that the polymer-supported catalyst is soluble in nonpolar solvents and insoluble in polar solvents. Using the supported rhodium catalysts, addition of aryl and vinylboronic acids to the electrophiles such as enones, aldehydes, N-sulfonyl aldimines, and alkynes occurs smoothly to provide products in high yields. Additions of terminal alkynes to enones and industrially relevant hydroformylation reactions have also been successfully carried out. Studies show that the leaching of Rh from the polymer support is low and catalyst recycle can be achieved by simple precipitation and filtration.

Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated ketones under microwave irradiation

The Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated cyclic ketones was studied under controlled microwave irradiation conditions. A variety of catalysts, bases and solvents was explored in order to achieve optimum yields in the sho