719-79-9

Usage

Synthesis Reference(s)

Synthetic Communications, 10, p. 939, 1980 DOI: 10.1080/00397918008061855

InChI:InChI=1/C16H18/c1-2-9-16(14-10-5-3-6-11-14)15-12-7-4-8-13-15/h3-8,10-13,16H,2,9H2,1H3

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 541-33-3 1,1-dichlorobutane 
• 1726-14-3 1,1-diphenyl-1-butene 
• 7495-83-2 n-butyl diphenylmethyl ether 
• 10557-57-0 propylmagnesium iodide 
• 5331-17-9 1,1-diphenylbutan-1-ol 
• 29949-16-4 2,2’-diphenylpentanenitrile 
• 861777-12-0 2-benzhydryl-1-phenyl-butan-1-one 
• 123-72-8 butyraldehyde 
• 71-43-2 benzene 
• 616-21-7 1,2-dichlorobutane 
• 75-77-4 chloro-trimethyl-silane 
• 85316-36-5 4,4-diphenylbutyllithium 

Downstream Products

• 54890-00-5 1,1-dicyclohexyl-butane 
• 854458-55-2 1,1-bis-(4-nitro-phenyl)-butane 
• 3370-19-2 4,4-Diphenyl-8-diethylamino-octin-⁽⁶⁾ 
• 6431-56-7 4,4,9,9-Tetraphenyl-dodecan 
• 6393-07-3 1,2,2-Triphenyl-pentan 
• 6393-06-2 1,3,3-Triphenyl-hexan 
• 69318-56-5 1,1-bis-(4-amino-phenyl)-butane 

Relevant academic research and scientific papers

Ligand-Enabled Nickel-Catalyzed Redox-Relay Migratory Hydroarylation of Alkenes with Arylborons

A redox-relay migratory hydroarylation of isomeric mixtures of olefins with arylboronic acids catalyzed by nickel complexes bearing diamine ligands is described. A range of structurally diverse 1,1-diarylalkanes, including those containing a 1,1-diarylated quaternary carbon, were obtained in excellent yields and with high regioselectivity. Preliminary experimental evidence supports the proposed non-dissociated chainwalking of aryl-nickel(II)-hydride species along the alkyl chain of alkenes before selective reductive elimination at a benzylic position. A catalyst loading as low as 0.5 mol % proved to be sufficient in large-scale synthesis while retaining high reactivity, highlighting the practical value of this transformation.

Photochemical Nickel-Catalyzed Reductive Migratory Cross-Coupling of Alkyl Bromides with Aryl Bromides

A novel method to access 1,1-diarylalkanes from readily available, nonactivated alkyl bromides and aryl bromides via visible-light-driven nickel and iridium dual catalysis, wherein diisopropylamine (iPr2NH) is used as the terminal stoichiometric reductant, is reported. Both primary and secondary alkyl bromides can be successfully transformed into the migratory benzylic arylation products with good selectivity. Additionally, this method showcases tolerance toward a wide array of functional groups and the presence of bases.

Ligand-Controlled Nickel-Catalyzed Reductive Relay Cross-Coupling of Alkyl Bromides and Aryl Bromides

1,1-Diarylalkanes are important structural frameworks which are widespread in biologically active molecules. Herein, we report a reductive relay cross-coupling of alkyl bromides with aryl bromides by nickel catalysis with a simple nitrogen-containing ligand. This method selectively affords 1,1-diarylalkane derivatives with good to excellent yields and regioselectivity.

Polysilane-supported transition metal catalyst for liquid phase reaction

The present invention provides a polysilane-supported transition metal catalysts or a polysilane/inorganic compound-supported transition metal catalysts, wherein various types of transition metals are supported by polysilane compounds, or combination of polysilanes and inorganic compounds. The catalysts of the present invention are hardly soluble in hydrocarbons and alcohols and are useful as catalysts in heterogeneous system for various organic synthetic reactions using the above solvents. Polysilanes supporting transition metals are easily crosslinkable by thermal treatment, microwave irradiation, UV irradiation or chemical methods such as hydrosilylation reaction and are changed to be insoluble in various solvents keeping high catalytic activity. Moreover, the stability and operability of polysilane-supported transition metal catalysts will be improved by the support thereof on inorganic compounds. These polysilane-supported transition metal catalysts show a high catalytic activity in hydrogenation reaction, hydrosilylation reaction, Heck reaction, Suzuki-Miyaura coupling reactions and the like. The catalyst is easily recoverable and reusable and the leakage of metals is extremely few.

Zinc chloride enhanced arylations of secondary benzyl trifluoroacetates in the presence of b-hydrogen atoms

Zinc or swim: Arylation of benzyl trifluoroacetates with arylzinc reagents in the presence of β- hydrogen atoms were realized under mild conditions. Both electron-rich and electron-deficient arene substrates were successfully arylated. This arylation method could offer a very versatile synthetic route to access a series of diversity-oriented diarylalkane motifs. TFA = trifluoroacetyl. Copyright

Polysilane-supported Pd and Pt nanoparticles as efficient catalysts for organic synthesis

Polysilane-supported Pd and Pt catalysts have been prepared for the first time, and used successfully in hydrogenation, Suzuki and Sonogashira reactions, and hydrosilylation respectively: the reactions proceeded in high yields, and the catalysts could be recovered almost quantitatively by simple filtration and reused. The Royal Society of Chemistry 2006.

Polyethylene glycol mediated reductive decyanation of diphenylacetonitrile moderately enhanced by microwave heating

An efficient and clean procedure for the preparation of alkyldiphenylmethanes and 4,4-diphenylbutylamines from their corresponding nitriles by using sodium hydroxide-polyethylene glycol reagent system in a domestic microwave oven is described. The products are isolated by simple aqueous work up in excellent yields.

Kinetics and equilibrium constants for reactions of α-phenyl- substituted cyclopropylcarbinyl radicals

Laser-flash photolysis methods were used to determine Arrhenius functions for cyclizations of the 4,4-diphenyl-3-butenyl (2) and trans-4- phenyl-3-butenyl (5) radicals to the 1,1-diphenylcyclopropylcarbinyl (1) and 1-phenylcyclopropylcarbinyl (4) radicals, respectively. At 20 °C, the cyclization rate constants are 1.7 x 107 and 5.4 x 106 s-1. Equilibrium constants for the two processes were estimated and evaluated with thermochemical data and via computational methods, and Arrhenius functions for the ring-opening reactions of the cyclopropylcarbinyl radicals were calculated. The cyclization reactions of 2 and 5 are strongly enthalpy controlled. Production of radicals 1 and 2 from the corresponding tert- butylperoxy esters in the presence of Et3SnH gave diphenylcyclopropylmethane and 1,1-diphenyl-1-butene from H-atom trapping of radicals 1 and 2 and 4- phenyl-1,2-dihydronaphthalene which derives from the product radical formed by addition of the radical moiety in 2 to the cis-phenyl group. Rate constants for the latter cyclization of 2 and for reactions of radicals 1 and 2 with Et3SnH were obtained from the indirect kinetic studies.

Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones

Irradiation of O-acyl derivatives 1 of N-hydroxy-2-thiopyridone with visible light in the presence of phenyl vinyl sulphone or vinyl triphenylphosphonium bromide leads to the corresponding adducts 8 and 9 which can undergo a wide variety of further transformations.

Reactions of O,O-Diprotonated Nitro Olefins with Benzenes. Formations of Phenylacetones, 4H-1,2-Benzoxazines and Biarylacetone Oximes

O,O-Diprotonated nitro olefins undergo three alternative electrophilic reactions which yield α-phenylacetones, 4H-1,2-benzoxazines and biphenylacetone oximes depending on the reaction conditions (temperature and time) and aromatic substrates.Although these reactions are seemingly divergent, a common intermediate of a phenylated protonated aci-nitro species, derived from the dication, is postulated to be involved in the reactions.Furthermore, the formation of benzoxazines and biphenylacetone oximes can be interpreted in terms of participation of novel chemical species with phenylethylene dication character derived from the common intermediate.