Catalytic Friedel-Crafts Acylation of Aniline Derivatives

Advanced Synthesis and Catalysis

Volumn 343, Issue 1, 2001, Pages 71-74

  Kobayashi, Shu ^a   Komoto, Ichiro ^a   Matsuo, Jun Ichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aryl ketones; Friedel Crafts acylation; Gallium; Homogeneous catalysis; Lewis acids; Solvent systems

Indexed keywords

EID: 0002425320     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010129)343:1<71::AID-ADSC71>3.0.CO;2-J     Document Type: Article

References (47)

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36. Although acylation using excess polyphosphoric acid (PPA) was reported, substrates were limited; (a) D. A. Denton, H. Suschitzky, J. Chem. Soc. 1965, 4741; (b) B. Staskun, J. Org. Chem. 1964, 29, 2856.
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38. 3 to afford the corresponding aromatic ketone in 72% yield; (a) G. A. Olah, O. Farooq, S. M. F. Farnia, J. A. Olah, J. Am. Chem. Soc. 1988, 110, 2560; (b) G. A. Olah, US Patent 5,110,778, 1992 [Chem Abstr. 1998, 109, 57031.
39. 3 to afford the corresponding aromatic ketone in 72% yield; (a) G. A. Olah, O. Farooq, S. M. F. Farnia, J. A. Olah, J. Am. Chem. Soc. 1988, 110, 2560; (b) G. A. Olah, US Patent 5,110,778, 1992 [Chem Abstr. 1998, 109, 57031.
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41. Semi-empirical calculations of the electron density also supported these results.
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45. a value: MsOH (-1.9); AcOH (4.76).
46. Y. Sakata, T. Hashimoto, Yakugaku Zasshi 1959, 79, 881.
47. Physical data of other acylation adducts are shown in Supporting Information.