36047-01-5

Upstream product

• 536-74-3 phenylacetylene 
• 3218-36-8 4-Phenylbenzaldehyde 
• 591-50-4 iodobenzene 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 98-86-2 acetophenone 
• 98-80-6 phenylboronic acid 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 24721-26-4 4-chlorochalcone 
• 22966-09-2 (2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 13026-23-8 (2E)-3-(1,1'-biphenyl-4-yl)acrylic acid 
• 611-73-4 Benzoylformic acid 
• 1591-31-7 4-iodo-biphenyl 

Downstream Products

• 102477-83-8 3-([1,1′-biphenyl]-4-yl)-1-phenylpropan-1-one 
• 1242046-62-3 C₃₅H₂₆O₃ 
• 1242046-45-2 C₃₅H₂₆O₃ 
• 1236384-48-7 N-(3-benzyl-4-(biphenyl-4-yl)-2-oxo-6-phenyl-3,4-dihydro-2H-pyran-3-yl)benzamide 
• 139435-55-5 4-phenylchalcone-4'-sulfonyl chloride 
• 1283749-77-8 N-(1-([1,1'-biphenyl]-4-yl)-2-chloro-3-oxo-3-phenylpropyl)-4-methylbenzenesulfonamide 
• 1258526-07-6 2-(3-(biphenyl-4-yl)-1-phenylallylidene)hydrazinecarboximidamide 
• 1246850-27-0 N-((1R,2R)-1-(biphenyl-4-yl)-2-bromo-3-oxo-3-phenylpropyl)-4-methylbenzenesulfonamide 
• 1237542-73-2 3n-rac 

Relevant academic research and scientific papers

Sequential coupling-isomerization-coupling reactions - A novel three-component synthesis of aryl chalcones

Bromoaryl boronates bear a halide and a dormant organometallic functionality and, therefore, are perfectly suited for sequentially Pd-catalyzed reactions. The microwave-accelerated consecutive reaction of bromoaryl boronates, (hetero)aryl propargyl alcoho

1-Arylvinyl formats: A New CO Source and Ketone Source in Carbonylative Synthesis of Chalcone Derivatives

1-Arylvinyl formates as a kind of new CO surrogate have been explored for the first time. Most of the known CO precursors usually produce undesired residuals, which have to be removed. In this strategy, after CO release, the in situ generated acetophenones from 1-arylvinyl formates can be successfully applied as a good ketone source in the synthesis of chalcones with benzaldehydes via a palladium-catalyzed reductive carbonylation reaction. A variety of chalcones were isolated in satisfactory to good yields with good substrates compatibilities under mild conditions.

Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones

A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.

Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes

Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.

Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System

A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.

Pd/Indanone-Based Ligands: An Efficient Catalyst System for Ullmann-Type, Suzuki-Miyaura, and Mizoroki-Heck Cross-Coupling Reactions with Aryl Tosylates and Aryl Halides

2-Hydroxyindan-1-ones have been efficiently synthesized and successfully applied as ligands in Pd-catalyzed Ullmann type, Suzuki-Miyaura, and Mizoroki-Heck cross-coupling reactions with aryl tosylates and aryl halides. The ligands are air- and moisture-stable and have shown high catalytic activity with Pd(OAc) 2 in these cross-coupling reactions. The system tolerates a variety of functional groups in the product and can be re-used at least three times with maximum efficiency..

Coumarin based novel ligands in the Suzuki–Miyaura and Mizoroki–Heck cross-couplings under aqueous medium

Coumarin-based novel ligands (benzylidine-bis-(4-hydroxycoumarin)-diethylamines) were easily synthesized using 4-hydroxycoumarin, aromatic aldehydes, and diethylamine. The ionic ligand structure was established by X-ray study. They are air and moisture stable ligands and have shown highly efficient catalytic activity with Pd(OAc)2(0.1 mol % loading) in the Suzuki–Miyaura and (0.3 mol % loading) in the Mizoroki–Heck cross-coupling reactions in water or water/ethanol mixture. Pd-catalyst was reused efficiently without affecting variety of functional groups in the reaction.

Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction

The Kumada-Corriu reaction is a powerful tool for C-C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent. The mechanistic reason for the effectiveness of this strategy is uncovered by continuous-infusion ESI-MS studies.

Polyaniline coated on celite, a heterogeneous support for palladium: Applications in catalytic Suzuki and one-pot Suzuki-aldol reactions

Particles of celite were coated with polyaniline, characterized and used as a support for heterogenization of palladium metal ions. The prepared heterogeneous palladium catalysts were screened for Suzuki-Miyaura and one-pot Suzuki-aldol reactions with high conversions. The process of heterogenization on celite reduces the PANI consumption ten-fold when anchoring palladium ions onto the support. The recyclable catalyst was also used for the sunlight mediated Suzuki-Miyaura reaction with good conversion.

Multicomponent Cascade Synthesis of Biaryl-Based Chalcones in Pure Water and in an Aqueous Micellar Environment

The challenging multicomponent cascade synthesis of biaryl-based chalcones was carried out in pure water and in an aqueous micellar system. The first step of the protocol was a simple Pd-catalysed, ligand-free, and aerobic Suzuki–Miyaura reaction in aqueous medium. This proved to be extremely efficient for the coupling of aryl and heteroaryl bromides with different arylboronic acids. Subsequently, the resulting intermediates underwent an in-situ aldol condensation reaction to give biaryl(hetero)chalcones in good to excellent yields. When the protocol was applied to highly lipophilic or less reactive reagents, micellar catalysis was required for good results. To achieve this, we successfully used a new surfactant obtained from renewable resources that we recently designed. Furthermore, using this additive, the catalytic system can be repeatedly recycled without significant loss of activity.