Diaryl ketone arene

Arenes add to nitriles in the presence of a palladium catalyst in DMSO/trifluor-oacetic acid to give a diaryl ketone. ... 

Reaction of arenes with PhCCb, in an ionic liquid ( A -butylpyridinium chloroalumi-nate) gives diaryl ketones. ... 

Triethylsilane in trifluoroacetic acid has proved to be a mild and selective reducing agent for the conversion of aryl and diaryl ketones into the corresponding arenes however, with activated benzaldehydes, e.g, 4-MeCeH4-CHO, Friedel-Crafts alkylation competes with reduction. Reduction of phenyl cyclobutyl ketone and phenyl cyclopropyl ketone gives low yields (36 and ca. 25%, respectively) of the corresponding benzylcycloalkanes [the former reaction also affords phenylcydo-pentane (ca. 42%) via ring-expansion] and with ortAo-benzoylbenzoic acid and 3-benzoyIpropanoic acid the lactones (11) (100%) and (12) (86%), respectively, are formed. ... 

The AICI3-mediated chlorocarbonylation of arenes with oxalyl chloride has been used in the preparation of symmetrical and unsymmetrical diaryl ketones 1266 [945, 946],... 

Under Friedel-Crafts conditions (AICI3, CS2), oxalyl chloride reacts with aromatic hydrocarbons to give carbonyl chlorides, which are hydrolyzed by water to give carboxylic acids. The AICI3-mediated chlorocarbonylation of arenes with oxalyl chloride has been used in the preparation of symmetrical and unsymmetrical diaryl ketones [946] (see also Section 4.3.6). 

A related approach involves the direct decarbonylation of stable ketones. DauguUs and Brookhart demonstrated that the rhodium-catalyzed decarbonylation of diaryl ketones was feasible [11]. Efficient extrusion of CO from alkyl aryl ketones to form alkylarenes was easily achieved by rhodium(I) catalysis directed by apyridyl ortho to the RCO group (Scheme 22.6) [12]. (CO)2Rh(acac) was found to be the optimal catalyst and the methodology had a broad substrate scope. This method offers an alternative way to synthesize alkyl benzenes through an ARCIS reaction, complementary to the known Friedel-Crafts alkylation reaction of arenes. 

Mechanistic studies with sulphonium salts concern decomposition kinetics in hydroxylic solvents H- H exchange of the a-protons of methyl and allyl-sulphonium salts, the relative rates of which are strongly dependent upon both solvent and micellar effects radical chain reactions of triarylsulphonium halides and sodium alkoxides, which lead to arenes, anisoles, diaryl sulphides, and aldehydes or ketones and the catalysis of hydrocarbon autoxidation by... 

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