Catalyzed Friedel-Crafts Reaction Research Articles

Studies on Novel Synthetic Methodologies. Part 62. Fe3+‐K‐10 Montmorillonite Clay Catalyzed Friedel—Crafts Reaction of Unactivated Baylis—Hillman Adducts: An Efficient Stereoselective Synthesis of Trisubstituted Alkenes Containing a Benzyl Substituent.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Fe3+-K-10 Montmorillonite Clay Catalyzed Friedel–Crafts Reaction of Unactivated Baylis–Hillman Adducts: An Efficient Stereoselective Synthesis of Trisubstituted Alkenes Containing a Benzyl Substituent

Abstract The stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent has been achieved by employing Friedel–Craft reaction of aromatic compounds with unactivated Baylis–Hillman adducts in the presence of Fe3+-K-10 montmorillonite clay as a heterogeneous catalyst. The catalyst can be recovered and reused.

Ytterbium Triflate Catalyzed Friedel—Crafts Reaction: Facile Synthesis of Diaryl Ketones.

Abstract Friedel–Crafts reaction of aromatic compounds (benzenes, thiophene, furan, pyrrole, naphthalene, and benzothiophene) with bis(trichloromethyl) carbonate [BTC] was efficiently catalyzed by ytterbium triflate [Yb(OTf)3] to give diaryl ketones with moderate to good yields.

Ytterbium Triflate Catalyzed Friedel–Crafts Reaction: Facile Synthesis of Diaryl Ketones

Friedel–Crafts reaction of aromatic compounds (benzenes, thiophene, furan, pyrrole, naphthalene, and benzothiophene) with bis(trichloromethyl) carbonate [BTC] was efficiently catalyzed by ytterbium triflate [Yb(OTf)3] to give diaryl ketones with moderate to good yields.

Intramolecular Catalytic Friedel—Crafts Reactions with Allenyl Cations for the Synthesis of Quinolines and Their Analogues.

AbstractFor Abstract see ChemInform Abstract in Full Text.

In(OTf)3‐Catalyzed Friedel—Crafts Reaction of Aromatic Compounds with Methyl Trifluoropyruvate in Water.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Designing New α,β‐Unsaturated Thioesters for the Catalytic, Enantioselective Friedel—Crafts Alkylation of Indoles.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Lewis Acid BF3×OEt2‐Catalyzed Friedel—Crafts Reaction of Methylenecyclopropanes with Arenes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

In(OTf)3-Catalyzed Friedel-Crafts Reaction of Aromatic Compounds with Methyl Trifluoropyruvate in Water

In the presence of In(OTf) 3 as a catalyst, aniline derivatives la-c, 1e-h and anisole derivatives 2a-c, 2e reacted with methyl trifluoropyruvate 3 in water at room temperature to give the corresponding Friedel-Crafts reaction products 4a-g and 5a-d in good yields, respectively.

Designing New α,β‐Unsaturated Thioesters for the Catalytic, Enantioselective FriedelCrafts Alkylation of Indoles

AbstractA new class of α,β‐unsaturated S‐(1,3‐benzoxazol‐2‐yl) thioesters of type 2 have been synthesized and effectively employed as electrophiles in the stereoselective alkylation of indoles. The combination of electronic as well as steric properties of such Michael acceptors allowed us to carry out FriedelCrafts alkylations of various substituted indoles in the presence of a catalytic amount (20 mol‐%) of chiral cationic [PdII(Tol‐binap)] complexes. With the optimized catalytic system (PdCl2(MeCN)2/Tol‐binap/AgSbF6), the desired β‐indolyl‐substituted thioderivatives 4 were obtained in good yield, with an enantiomeric excess (ee) of up to 86%. The remarkable versatility of the enantiomerically enriched thioesters 4 was demonstrated by quantitatively transforming them into optically active β‐indolyl esters and amides under mild conditions. With this stereoselective, catalytic FriedelCrafts reaction, we open up the way towards new α,β‐unsaturated compounds that could be suitable candidates for the preparation of a number of optically active β‐substituted carboxylic compounds.

Synthesis of 4-phenyltetralone derivatives and reaction mechanism.

4-(p-Chlorophenyl)tetralone (6) and 7-chloro-5-(p-chlorophenyl)tetralone (9) are key intermediates for the development of benzazepinone derivative haftens. These compounds could be synthesized from 4-phenyltetralone derivatives by triflic acid catalyzed Friedel-Crafts reaction. The reaction mechanism of Friedel-Crafts alkylation/acylation with lactones in triflic acid is presented. According to our tentative research, ring opening of protonated lactone (2) occurs in alkyl cleavage and the rate of the reaction is not dependent on concentration of triflic acid. So, alkylation of lactone in Friedel-Crafts reaction is presumed to be A(AL)1. In second step, intramolecular acylation of the intermediates 4 to 6, 4 can be transformed to a triflic acid-carboxylic anhydride and then the cyclization is undergone after leaving of the triflate anion.

Epoxide formation in the Friedel-Crafts reaction of adipoyl chloride and bromobenzene

The aluminium chloride catalysed Friedel-Crafts reaction between adipoyl chloride and bromobenzene has been re-examined. At elevated temperatures a number of side products are produced including a cyclopentane epoxide. The structure of this epoxide was elucidated by nmr and ir spectroscopy and its stereochemistry confirmed by x-ray crystallography.

Friedel-Crafts reactionin fluorous fluids

The scope and utility of fluorous (perfluorinated) fluids as reaction media for Lewis acid catalyzed Friedel-Crafts reaction are described.

On the transition state for “clayzic”-catalyzed Friedel-Crafts reactions upon anisole

The activation parameters point to strongly organized transition state on the catalyst surface, partial breaking of the carbon-leaving group bond in the BnCl or in the Ac 2O reagent.

Chlorination and bromination of fullerenes. Nucleophilic methoxylation of polychlorofullerenes and their aluminum trichloride catalyzed Friedel-Crafts reaction with aromatics to polyarylfullerenes

Chlorination and bromination of fullerenes. Nucleophilic methoxylation of polychlorofullerenes and their aluminum trichloride catalyzed Friedel-Crafts reaction with aromatics to polyarylfullerenes

Aluminum Chloride Catalyzed Friedel-Crafts Reaction of Anisole with Epoxide Accompanying Isomerization

Abstract The reaction of anisole with propylene oxide by aluminum chloride has been studied in various kinds of solvents. While the normal Friedel-Crafts reaction yielded 2-(methoxyphenyl)-1-propanols, 1,1-bis(methoxyphenyl)-propanes were also formed in this reaction; these were not obtained by the subsequent reaction of mono(methoxyphenyl) products with another anisole. The yields of 1,1-bis(methoxyphenyl)propanes increased by increasing the basicity of solvents. The mechanism of the formation of 1,1-bis(methoxyphenyl)propanes can be explained by the isomerization of epoxide to aldehyde and the subsequent condensation with anisole. Various kinds of epoxides also gave 1,1-bis(methoxyphenyl)alkanes in nitromethane.