604007-06-9

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• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 495-41-0 1-phenylbut-2-en-1-one 
• 52755-38-1 1-phenyl-2-buten-1-ol 
• 108-86-1 bromobenzene 

Relevant academic research and scientific papers

Synthesis and Evaluation of Azolium-Based Halogen-Bond Donors

A method for the synthesis of iodinated imidazolium and triazolium N-heterocyclic halogen-bond-donor catalysts has been developed. This approach was applied to the synthesis of a variety of 1,2,4-triazolium salts to prepare a series of novel chiral haloge

NMR spectroscopic characterization and DFT calculations of zirconium(IV)-3,3′-Br2a-BINOLate and related complexes used in an enantioselective friedela-crafts alkylation of indoles with α,β-unsaturated ketones

Experimental and theoretical studies on the structure of several complexes based on (R)-3,3′-Br2a-BINOL ligand and group (IV) metals used as catalysts in an enantioselective Friedela-Crafts alkylation of indoles with α,β-unsaturated ketones have been carried out. NMR spectroscopic studies of these catalysts have been performed, which suggested that at room temperature the catalysts would form a monomeric structure in the case of TiIV and a dimeric structure in the cases of ZrIV and HfIV. Density functional theory (DFT) calculations clearly corroborate the conclusions of these experimental spectroscopic studies. The dimeric structure with a doubly bridged motif [ZrIV 2(μ-(R)-3,3′-Br2a-BINOL)2] where each binaphthol ligand acts as bridge between the metal centers (Novaks model) is more stable than the dimeric structure with a doubly bridged motif [Zr IV2(μ-OtBu)2] where the tert-butoxide groups act as bridging ligands (Kobayashis model). The scope of the Friedela-Crafts alkylation with regard to the indole structure has been studied. Finally a plausible mechanism for the Friedela-Crafts reaction and a stereomodel for the mode of action of the catalyst that explain the observed stereochemistry of the reaction products have been proposed.

Highly enantioselective friedel-crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes

Complexes of BINOL-based llgands with Zr(OtBu)4 catalyze the Frledel-Crafts alkylatlon reaction of Indoles and pyrrole with nonchelating β-substituted α,β-enonee at room temperature affording the expected products with good yields an

Chiral tetra-coordinate aluminum cation in catalysis

Although the application of cationic aluminum complexes in catalysis has been extensively investigated, the incorporation of an aluminum cation into a chiral environment is less explored. In this study, a C2-symmetric chiral tetra-coordinate aluminum cation [3]+ bearing two chiral amino alcohol-derived ligands was prepared from commercially available starting materials in two steps. The high Lewis acidity of [3]+ exceeding that of B(C6F5)3 was verified by a competition binding experiment. Preliminary catalytic activity studies of [3]+ revealed that the tetra-coordinate aluminum cation is effective in accomplishing high conversion in all cases. However, the presence of a labile N?Al bond diminishes the enantioselectivity of the activation process.

Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones

Chiral [Al(salen)Cl] complex (10 mol%) in the presence of 2,6-lutidine (10 mol%) was found to be effective in catalysing the enantioselective Friedel-Crafts-type conjugate addition of indoles (3) to (E)-arylcrotyl ketones (2), furnishing the corresponding

Hydrogen-Bonding-Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water

Metal-bound water molecules have recently been recognized as a new facet of soft Lewis acid catalysis. Herein, a chiral palladium aqua complex was constructed that enables carbon–hydrogen bonds of indoles to be functionalized efficiently. We embraced a ch

Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications

A new method of synthesis of an analogue of Bolm's 2,2′-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (>96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents. (Figure presented.).

The combined use of cationic palladium(II) with a surfactant for the C-H functionalization of indoles and pyrroles in water

The utility of electrophilic palladium(II) species was demonstrated for C-H bond functionalization of indoles and pyrroles in water. The system displayed attractive features that are reminiscent of both precious-metal catalysis and micellar catalysis.

Enantioselective synthesis of substituted indoles through zirconium(IV)-catalyzed Friedel-Crafts alkylation

The chiral complex of (R)-3,3-BrBINOL and zirconium tert-butoxide catalyzes the Friedel-Crafts alkylation of indoles with enones bearing an alkyl or fluorinated group at the β-position to give indoles having a side chain at the C3 position with a tertiary

Chiral Bronsted acid catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones: Short access to optically active 2- and 3-substituted indole derivatives

The asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones catalyzed by chiral phosphoric acid is reported. A wide range of indoles and 4,7-dihydroindoles were allowed to react with α,β-unsaturated ketones to give the corres