779-51-1

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 1662, 1975 DOI: 10.1021/jo00899a039Synthetic Communications, 13, p. 87, 1983 DOI: 10.1080/00397918308061963Tetrahedron Letters, 23, p. 1979, 1982 DOI: 10.1016/S0040-4039(00)87238-X

InChI:InChI=1/C15H14/c1-13(15-10-6-3-7-11-15)12-14-8-4-2-5-9-14/h2-12H,1H3/b13-12+

Upstream product

• 917-64-6 methyl magnesium iodide 
• 5342-87-0 1,2-diphenylpropane-2-ol 
• 60-29-7 diethyl ether 
• 3360-53-0 1-bromo-2-phenyl-1-propene 
• 103-79-7 1-phenyl-acetone 
• 451-40-1 phenyl benzyl ketone 
• 74-88-4 methyl iodide 
• 948-97-0 2,3-diphenyl-1-propene 
• 1083-98-3 diisopropyl benzylphosphonate 
• 98-86-2 acetophenone 
• 886-38-4 diphenylcyclopropenone 
• 936-51-6 2-phenyl-1,3-dioxolane 
• 3674-77-9 2-methyl-2-phenyl-1,3-dioxolane 
• 41997-47-1 1,1-diphenyl-2-propanol 

Downstream Products

• 5809-65-4 3,4-diphenyl-but-3-enoic acid 
• 51507-26-7 acetic acid-((1RS,2SR)-1-methyl-2-nitro-1,2-diphenyl-ethyl ester) 
• 70671-91-9 3-bromo-1,2-diphenyl-propene 
• 833-81-8 (E)-1,2-diphenylpropene 
• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 
• 3558-63-2 2,3,4,6-tetraphenylpyridine 
• 19643-70-0 (2R)-propane-1,2-diyldibenzene 
• 19643-68-6 (2S)-propane-1,2-diyldibenzene 
• 883-20-5 9-methylphenanthrene 
• 24471-57-6 9-bromomethylphenantrene 
• 100-52-7 benzaldehyde 
• 832-69-9 1-methylphenanthrene 
• 106403-99-0 (E)-1,1'-<1-(Bromomethyl)-1,2-ethenediyl>bis 

Relevant academic research and scientific papers

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C[sbnd]C cross-coupling reactions

Improving carbon–carbon cross-coupling reactions is an ongoing process and finding the most versatile and stable catalyst precursors has been of great interest. Ligand design has been proven to be important since it is responsible for providing electron density and steric saturation around the metal centre, thus contributing towards the stereo-electronic properties. The adamantyl moiety has been used to generate highly bulky and electron-rich ligands for application in palladium-catalysed cross-coupling reactions. Accordingly, we have prepared some Schiff-base adamantyl ligands (L1-L3) and complexed them with [PdCl2(MeCN)2] to afford the (pre)catalysts C1-C3, which were successfully applied in Mizoroki-Heck and Suzuki-Miyaura carbon–carbon cross-coupling reactions. The cross-coupling reaction products were obtained in good yields using 0.5 mol % Pd catalyst loading. C2 and C3 showed remarkable activity in the Mizoroki-Heck coupling reactions involving substrates with substituents on the olefin and aryl halide (including 4-Cl, 4-CH3, -CO2Me and -CO2Et). We also, observed that the Suzuki-Miyaura cross-coupling system was active towards challenging activated and deactivated aryl chlorides, with to up 70% conversions recorded. The mercury poisoning tests conducted revealed that the catalysts act as homogenous molecular active species in the Mizoroki-Heck reactions and act as both homogenous and heterogeneous catalysts in the Suzuki-Miyaura cross-coupling reactions.

Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences

Energy-transfer processes involving copper complexes are rare. Using an optimized heteroleptic copper complex, Cu(bphen)(XantPhos)BF4, photosensitized E → Z isomerization of olefins is demonstrated. The XantPhos ligand afforded sensitizers with improved catalyst stability, while the bphen ligand lengthened the excited-state lifetime. A series of 25 di- and trisubstituted alkenes underwent photoisomerization, including macrocycles and 1,3-enynes. Cu(bphen)(XantPhos)BF4 could also be employed in a tandem ATRA/photoisomerization process employing arylsulfonyl chlorides, an example of photoisomerization with halide-substituted olefins.

Highly Stereoselective Positional Isomerization of Styrenes via Acid-Catalyzed Carbocation Mechanism

The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Br?nsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this protocol is further highlighted by the gram-scale synthesis, high stereoselectivity, good functional group tolerance, and simple operation. Mechanistic studies support that Al(OTf)3 acts as a hidden Br?nsted acid catalyst and a carbocation intermediate is formed.

Remote sp2C-H Carboxylation via Catalytic 1,4-Ni Migration with CO2

A remote catalytic reductive sp2 C-H carboxylation of arenes with CO2 (1 bar) via 1,4-Ni migration is disclosed. This protocol constitutes the first catalytic 1,4-Ni migration reported to date, thus offering new vistas in the Ni-catalyzed reductive coupling arena while providing an unconventional new platform for incorporating electrophilic sites at remote sp2 C-H linkages.

Nickel-Catalyzed Allylmethylation of Alkynes with Allylic Alcohols and AlMe3: Facile Access to Skipped Dienes and Trienes

We present herein an unprecedented allylative dicarbofunctionalization of alkynes with allylic alcohols. This simple catalytic procedure utilizes commercially available Ni(COD)2, triphenylphosphine, and inexpensive reagents, and delivers valuable skipped dienes and trienes with an all-carbon tetrasubstituted alkene unit in a highly stereoselective fashion. Preliminary mechanistic studies support the reaction pathway of allylnickelation followed by transmetalation in this dicarbofunctionalization of alkynes.

Promising new catalytic properties of a Co (II)-carboxamide complex and its derived Co3O4 nanoparticles for the Mizoroki-Heck and the Epoxidation reactions

The new Co(II) - carboxamide complex (1) and Co3O4 nanoparticles (2), by way of thermal decomposition of (1) have been efficiently synthesised in the environment-friendly. X-ray diffraction reveals a slightly distorted octahedral coordination of cobalt (four nitrogens and two oxygens) in (1) and regular octahedral or tetrahedral ones (oxygens only) in (2). The investigation of (1) and (2) in the Mizoroki-Heck and epoxidation of alkens reactions showed them both to be powerful, green and inexpensive catalysts.

Synthesis of α-methylstilbenes using an aqueous Wittig methodology and application toward the development of potent human aromatase inhibitors

The development of aqueous Wittig methodology for the synthesis of α-methylstilbenes using tripropylphosphine-derived phosphonium salts is described. The Wittig olefination reaction was high yielding and allowed isolation of stilbenes by simple filtration and washing with water. The novel phosphonium salts employed were accessed via a highly efficient, regioselective addition of hydrogen bromide to styrenes. Application of the α-methylstilbenes toward the synthesis of a collection of stilbenoid-triazoles is reported and their inhibition of CYP450 19A1 (aromatase) investigated. The overall structure-activity profile provided additional evidence on the aryl halide-ketone bioisostere hypothesis and identified 6c as a potent inhibitor of aromatase in vitro (Ki = 8 nM).

Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions

A method for the construction of boron-substituted quaternary carbons or diarylquaternary carbons by arylboration of highly substituted alkenylarenes is presented. A wide range of alkenes and arylbromides can participate in this reaction thus allowing for a diverse assortment of products to be prepared. In addition, a solvent dependent regiodivergent arylboration of 1,2-disubstituted alkenylarenes is presented, thus greatly increasing the scope of products that can be accessed.