7498-87-5

Usage

InChI:InChI=1/C16H14O/c17-16-14-9-5-4-8-13(14)10-11-15(16)12-6-2-1-3-7-12/h1-9,15H,10-11H2

Upstream product

• 2901-34-0 2,4-diphenylbutanoic acid 
• 133565-97-6 1-(1-phenylethenyl)benzocyclobuten-1-ol 
• 17215-80-4 2-chloro-1-tetralone 
• 60-12-8 2-phenylethanol 
• 140-29-4 phenylacetonitrile 
• 21460-77-5 2,4-diphenyl-butyryl chloride 
• 20985-27-7 2,4-diphenylbutanamide 
• 38858-72-9 1-trimethylsiloxy-3,4-dihydronaphthalene 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 108-86-1 bromobenzene 
• 4370-96-1 4-oxo-2,4-diphenylbutanoic acid 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1483-72-3 diphenyliodonium chloride 
• 20841-46-7 2-(phenylthio)-3,4-dihydronaphthalen-1(2H)-one 

Downstream Products

• 856082-35-4 1-ethyl-2-phenyl-1,2,3,4-tetrahydro-[1]naphthol 
• 1022-15-7 4-methyl-3-phenyl-1,2-dihydronaphthalene 
• 881851-79-2 (1S,2R)-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 104049-33-4 t.butyl-6 methyl-2 phenyl-2 tetralone-1 
• 104049-32-3 n-butyl-6 methyl-2 phenyl-2 tetralone-1 
• 20495-17-4 2-phenyl-1-tetralone oxime 
• 858439-03-9 (2-phenyl-3,4-dihydro-[1]naphthyl)-acetic acid 
• 861049-95-8 1-Hydroxy-1.2-diphenyl-1.2.3.4-tetrahydro-naphthalin 
• 426841-92-1 (1R,2S)-2-phenyl-1,2,3,4,-tetrahydronaphthalen-1-ol 

Relevant academic research and scientific papers

Base-controlled chemoselectivity: direct coupling of alcohols and acetonitriles to synthesise α-alkylated arylacetonitriles or acetamides

We achieved chemoselective synthesis of α-alkylated arylacetonitriles and acetamides by combining Ir complex-catalysed direct coupling of alcohols and nitriles by a simple adjustment of the base. Methanol and ethanol performed well as the alkylating reagents. This method of acetonitrile alkylation provided a novel approach for carbon chain extension.

Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System

A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines

An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.

Blue Light Promoted Difluoroalkylation of Aryl Ketones: Synthesis of Quaternary Alkyl Difluorides and Tetrasubstituted Monofluoroalkenes

A facile and cost-effective method for the preparation of fluoroalkylated compounds has been described by the direct photoexcitation of halofluoroalkanes with blue light absorptivity, enabling the difluoroalkylation of aryl ketones. The methodology has provided an efficient, mild, and catalyst-free synthetic method for quaternary difluoroalkylated arenes and tetrasubstituted monofluoroalkenes.

Enantioselective electrophilic fluorination of α-aryl-tetralones using a preparation of N-fluoroammonium salts of cinchonine

The enantioselective electrophilic fluorination of α-aryl-tetralones is promoted by cinchonine/selectfluor combinations. This strategy allows a facile synthesis of the corresponding 2-fluoro-2-aryl-1-tetralones with excellent yields (up to >98%) and moder

Atmosphere-Controlled Chemoselectivity: Rhodium-Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols

The chemoselective alkylation and olefination of alkylnitriles with alcohols have been developed by simply controlling the reaction atmosphere. A binuclear rhodium complex catalyzes the alkylation reaction under argon through a hydrogen-borrowing pathway and the olefination reaction under oxygen through aerobic dehydrogenation. Broad substrate scope is demonstrated, permitting the synthesis of some important organic building blocks. Mechanistic studies suggest that the alkylation product may be formed through conjugate reduction of an alkene intermediate by a rhodium hydride, whereas the formation of olefin product may be due to the oxidation of the rhodium hydride complex with molecular oxygen.

Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones

The transition-metal-catalyzed α-arylation of carbonyl compounds is a widely practiced method for C-C bond formation. Several enantioselective versions of this process have been reported, but intermolecular, enantioselective coupling reactions of aryl electrophiles with α-fluoro carbonyl compounds have yet to be disclosed. We report enantioselective coupling of aryl and heteroaryl bromides and triflates with α-fluoroindanones catalyzed by palladium complexes of a BINOL-derived monophosphine and Segphos, respectively. The enolates were generated directly from α-fluoroindanones in the presence of potassium phosphate base during the reactions. We also report that reactions of α-fluorotetralones occur in high yields and enantioselectivities when conducted with enolates generated by elimination of trifluoroacetate from trifluoromethyl β-diketone hydrates. These reactions were catalyzed by palladium complexes of the commercially available bisphosphine Difluorphos. Thus, the formation of enantioenriched α-aryl-α-fluoroketones can be readily achieved by C-C bond formation when the appropriate palladium catalyst and α-fluoro enolate precursor were used.

N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products

NHC-Pd(II)-Im complex 1 has proven to be an efficient catalyst in the reaction between tetralones 2 and aryl chlorides 3, giving the α-arylated tetralones 4 in good to high yields. In addition, if the above reaction mixture was exposed to air at room temp

Highly selective palladium-catalyzed direct c-h α-monoarylation of carbonyl compounds using water containing the surfactant polyoxyethylene- α-tocopheryl sebacate (PTS) as a solvent

Highly selective direct C-H α-monoarylation reactions of 4-chromanones, ketones and 2-phenylacetaldehyde with aryl halides have been performed in satisfactory yields by using a tris(dibenzylideneacetone) dipalladium(0)/tri-tert-butylphosphine tetrafluoroborate catalyst system, potassium bicarbonate as the base and a solvent consisting of pure water containing a small amount of polyoxyethylene-α-tocopheryl sebacate (PTS). Analogous reaction conditions have been employed in a tandem process leading to phenyl-substituted isocoumarins from carbonyl compounds and methyl 2-bromobenzoate.