Search results for "rafts"

ChemInform Abstract: Synthesis of Functionalized Indoles with an α-Stereogenic Ketone Moiety Through an Enantioselective Friedel-Crafts Alkylation wi…

2010

Chiral complexes of BINOL-based ligands with hafnium tert-butoxide catalyze the enantioselective Friedel-Crafts alkylation of indoles with (E)-1,4-diaryl-2-butene-1,4-diones at room temperature, with good yields and ee up to 94%. Hafnium(IV) was found to be a more effective Lewis acid than other frequently used metal ions such as titanium(IV) or zirconium(IV). Unlike the enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated compounds where the stereogenic center is generated in the β-position to a carbonyl group, the Friedel-Crafts alkylation with 2-butene-1,4-diones described here generates an α-stereogenic center with respect to one of the carbonyl groups. This can be…

Synthesis of Functionalized Indoles with an α-Stereogenic Ketone Moiety Through an Enantioselective Friedel-Crafts Alkylation with (E)-1,4-Diaryl-2-b…

2009

Chiral complexes of BINOL-based ligands with hafnium tert-butoxide catalyze the enantioselective Friedel-Crafts alkylation of indoles with (E)-1,4-diaryl-2-butene-1,4-diones at room temperature, with good yields and ee up to 94%. Hafnium(IV) was found to be a more effective Lewis acid than other frequently used metal ions such as titanium(IV) or zirconium(IV). Unlike the enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated compounds where the stereogenic center is generated in the β-position to a carbonyl group, the Friedel-Crafts alkylation with 2-butene-1,4-diones described here generates an α-stereogenic center with respect to one of the carbonyl groups. This can be…

New aromatic diamines containing a multiring flexible skeleton for the synthesis of thermally stable polyimides

2000

Abstract Multi-ring aromatic diamines bearing a long alkyl chain (C 6 , C 8 or C 16 ) were obtained from the corresponding dinitro compounds synthesized by a Friedel–Crafts alkylation of substituted mesitylenes by paranitrobenzyl chloride. The bismaleimide synthesized from the diamine bearing a C 16 chain formed a thermostable polyimide.

Synthesis of new soluble polybenzyls by Friedel-Crafts reactions

1999

Soluble polybenzyls were prepared by a catalytic electrophilic Friedel-Crafts type polycondensation between α,α'-dichloro-p-xylene and substituted (by an alkyl or an alkoxy side-chain) mesitylene. The influence of the length of the side-chain on the solubility of the polymer was examined. The polymers were found to be soluble in common organic solvents. Polymer characterizations were made by 13 C nuclear magnetic resonance spectroscopy (NMR), size exclusion chromatography (SEC), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and elemental analysis.

Enantioselective Synthesis of Substituted Indoles Through Zirconium(IV)-Catalyzed Friedel–Crafts Alkylation

2012

The chiral complex of ( R )-3,3′-Br 2 -BINOL 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 stereogenic center in good yields and with excellent enantioselectivities.

1975

In the polymerization of isobutene catalyzed by aluminium tribromide and in the polymerization of styrene catalyzed by trifluoromethanesulphonic acid it is supposed that an inactive catalyst monomer complex is formed which is in equilibrium with other active species. The monomer complexation of the catalyst explains the S-shaped conversion curves and the complex kinetics of the polymerization. The value of the equilibrium constant Km (complexation constant) expresses what part of the catalyst may take part in the polymerization process as an active initiating species. For the system isobutene/AlBr3, Km was found to be 0,62 1/mol. In the system styrene/CF3SO3H, the high value of the complexa…

Organocatalytic enantioselective aza-Friedel–Crafts reaction of 2-naphthols with benzoxathiazine 2,2-dioxides

2015

An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.

ChemInform Abstract: Organocatalytic Enantioselective Aza-Friedel-Crafts Reaction of 2-Naphthols with Benzoxathiazine 2,2-Dioxides.

2015

An organocatalytic enantioselective aza-Friedel–Crafts addition of 2-naphthols to benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional catalyst. The method allows the use of a wide range of aromatic compounds as nucleophiles, including 1-naphthol and sesamol, and benzoxathiazines 2,2-dioxides, expanding the existing state of the art enantioselective synthesis of aminomethylnaphthol derivatives.

ChemInform Abstract: Catalytic Enantioselective Friedel-Crafts Reactions of Naphthols and Electron-Rich Phenols

2016

The enantioselective Friedel–Crafts reaction is a powerful tool for the construction of benzylic stereocenters in a stereodefined manner. Significant advances have already been achieved with heteroarenes such as indoles and pyrroles; however, the reaction with homoarenes is less developed. This short review covers the most relevant literature on enantioselective Friedel–Crafts reactions with naphthols and phenols. 1 Introduction 2 Friedel–Crafts Reactions Involving 1,2-Nucleophilic Addition to C=X Bonds 3 Friedel–Crafts Reactions Involving Conjugate Nucleophilic Addition to Electrophilic C=C Bonds 4 Friedel–Crafts Reactions Involving π-Allylic Complexes as Electrophiles 5 ipso-Friedel–Craft…

ChemInform Abstract: Enantioselective Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones.

2009

The first catalytic enantioselective Friedel−Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3′-dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.