21847-94-9Relevant academic research and scientific papers
Lewis acid-catalyzed Friedel-Crafts acylation reaction using carboxylic acids as acylating agents
Kawamura, Masato,Cui, Dong-Mei,Hayashi, Teruyuki,Shimada, Shigeru
, p. 7715 - 7717 (2003)
Rare-earth metal Lewis acids, in particular Eu(NTf2) 3, were found to be efficient catalysts for Friedel-Crafts acylation reaction using aliphatic as well as aromatic carboxylic acids as acylating agents at high temperature.
Friedel-Crafts acylation reaction using carboxylic acids as acylating agents
Kawamura, Masato,Cui, Dong-Mei,Shimada, Shigeru
, p. 9201 - 9209 (2007/10/03)
Dehydrative Friedel-Crafts acylation reaction of aromatic compounds with carboxylic acids as acylating agents was investigated in the presence of Lewis acid- or Br?nsted acid-catalyst. Various metal triflates and bis(trifluoromethanesulfonyl)amides showed catalytic activity at high temperature, among which Eu(NTf2)3 proved to be the most effective and efficiently catalyzed the acylation reaction of alkyl- and alkoxybenzenes with aliphatic and aromatic carboxylic acids at 250 °C. Bi(NTf2)3 was more effective than Eu(NTf2)3 at lower temperature, but proved to be hydrolyzed in the presence of a small amount of water to give HNTf2 and [Bi6O4(OH)4(H2O)6](NTf2)6. The structure of the latter compound was confirmed by a single crystal X-ray analysis. Among five Br?nsted acids, HOTf, HNTf2, HCTf3, TsOH, and Nafion SAC-13, HNTf2 has proved to be the most efficient catalyst and more effective than Eu(NTf2)3 for the acylation of p-xylene with heptanoic acid at 220 °C or lower temperature. HNTf2 catalyzed the acylation of anisole with carboxylic acids in high yields in refluxing toluene with azeotropic removal of water.
