33093-76-4

Upstream product

• 558-13-4 carbon tetrabromide 
• 25871-56-1 diethoxy-phenyl-acetaldehyde 
• 88917-08-2 3,3-Dibrom-acrylsaeure-bromid 
• 71-43-2 benzene 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 100-42-5 styrene 
• 3740-49-6 1,1,1,3-tetrabromo-3-phenylpropane 
• 3876-61-7 1-benzoyl-2-bromoacetylene 
• 129993-18-6 1-vinyl-2-(1,1-biphenyl-4-yl)pyrrole 
• 288-13-1 NH-pyrazole 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 536-74-3 phenylacetylene 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 

Downstream Products

• 10250-60-9 1,5-dimethyl-3-phenyl-1H-pyrazole 
• 1226790-16-4 C₁₃H₁₄N₂ 
• 66870-43-7 1-methyl-5-(4-methylphenyl)-3-phenyl-1H-pyrazole 
• 53694-82-9 5-(4-chlorophenyl)-1-methyl-3-phenyl-1H-pyrazole 
• 66870-45-9 5-(4-methoxyphenyl)-1-methyl-3-phenyl-1H-pyrazole 
• 1188116-65-5 5-bromo-1-methyl-3-phenyl-1H-pyrazole 
• 19311-79-6 1-methyl-3,5-diphenyl-1H-pyrazole 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Relevant academic research and scientific papers

Synthesis of 2,2-di(pyrazol-1-yl)enones via the 2:1 coupling of pyrazoles and acylbromoacetylenes in solid alumina

Pyrazoles were reacted with acylbromoacetylenes in solid Al2O3 at room temperature to afford 2,2-di(pyrazol-1-yl)enones in 22–69% yield. The reaction proceeds via isolable intermediates, (Z)-2-bromo-2-(pyrazol-1-yl)enones. This unexpected 2:1 coupling is in contrast to similar reactions of pyrroles, furans and thiophenes, which give the corresponding acylethynyl derivatives. This reaction opens a one-pot route to inaccessible gem-dipyrazolylenones, which have potential applications as bidentate chelating ligands and building blocks for drug design.

Functionalized β,β-dichloroenones and β,β-dibromoenones as versatile building blocks: Synthesis and transformations

An efficient one-step synthesis of functionalized β,β-dichloroenones and β,β-dibromoenones was achieved via the Fe-catalyzed radical induced reaction between silyl enol ethers and carbon tetrachloride, bromotrichloromethane or carbon tetrabromide in moderate to good yields. This reaction proceeds through addition of the trichloromethyl or tribromomethyl radical group to the C[dbnd]C bond of the silyl enol ethers and subsequent base-induced elimination under mild conditions.

Access to gem-Dibromoenones Enabled by Carbon-Centered Radical Addition to Terminal Alkynes in Water Solution

We herein report a novel and more practical approach to prepare gem-dibromoenones from terminal alkynes, tetrabromomethane (CBr4), and water in a single step. Mechanistic studies reveal that the generation of a tribromomethyl radical with the assistance of a persulfate salt (K2S2O8) is essential to this transformation. The reaction features readily available chemicals, a broad substrate scope, a green solvent, and mild reaction conditions, providing an efficient alternative for construction of halogen-substituted enones.

Synthesis of 3-[5-(biphenyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones by palladium-free cross-coupling between pyrroles and haloalkynes on aluminum oxide

Cross-coupling of 2-(biphenyl-4-yl)pyrroles derived from 1-(biphenyl-4-yl)ethanone oximes and acetylene with 3-bromo-1-phenylprop-2-yn-1- one on aluminum oxide gave 3-[5-(biphe-nyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn- 1-ones in 35-46% yields.

[Cu(dap)2Cl] as an efficient visible-light-driven photoredox catalyst in carbon-carbon bond-forming reactions

Copper sees the light of day: [Cu(dap)2Cl] proved to be an excellent photoredox catalyst for atom-transfer radical addition reactions, as well as for allylation reactions (see scheme), providing an attractive alternative to commonly used iridium- and ruthenium-based catalysts. Copyright

The preparation of substituted pyrazoles from β,β-dibromo-enones by a tandem condensation/Suzuki-Miyaura cross-coupling process

Two consecutive tandem processes are described for the regioselective, two-step synthesis of 1,3,5-trisubstituted pyrazoles from α- hydroxyketones. The first, a tandem MnO2-mediated oxidation/Ramirez olefination reaction, provides a facile route to β,β-dibromo-enones. These valuable 1,3-dicarbonyl synthons can then be converted into 1,3,5-trisubstituted pyrazoles via a second tandem hydrazine condensation/Suzuki-Miyaura cross-coupling reaction. Using these procedures, a range of aryl and alkyl α-hydroxyketones have been transformed regioselectively into 1,3,5-trisubstituted pyrazoles. Georg Thieme Verlag Stuttgart.