Gallium(III) trifluormethanesulfonate: A water-tolerant, reusable Lewis acid catalyst for Friedel-Crafts reactions

G. K Surya Prakash, Ping Yan, Béla Török, I. Bucsi, Mutsuo Tanaka, George A. Olah

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The application of gallium(III) trifluoromethanesulfonate (triflate, OTf) in Friedel-Crafts alkylation and acylation reactions is described. Gallium triflate was found to be an excellent catalyst for the adamantylation of toluene with 1-bromoadamantane, where its activity was compared to that of well-known rare earth metal triflates. As Ga(OTf)3 does not decompose in the presence of water the isopropylation of aromatics can be carried out with isopropyl alcohol in moderate to excellent yields. While acetylation provides moderate yields in selective reactions, benzoylation of aromatics takes place in good yields in a catalytic and non-stoichiometric reaction. The catalyst can easily be recovered from the reaction mixture and can be reused without loss of activity, demonstrating its effective and environmentally friendly recyclable character.

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalCatalysis Letters
Volume85
Issue number1-2
DOIs
Publication statusPublished - Jan 2003

Fingerprint

Friedel-Craft reaction
Friedel-Crafts reaction
Lewis Acids
Gallium
gallium
Rare Earth Metals
catalysts
Acetylation
Acylation
acids
Catalysts
2-Propanol
Acids
Water
Alkylation
Toluene
water
Rare earths
Alcohols
acetylation

Keywords

  • Acylation
  • Alkylation with isopropyl alcohol
  • Environmentally benign catalysis
  • Gallium triflate
  • Regioselective adamantylation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Gallium(III) trifluormethanesulfonate : A water-tolerant, reusable Lewis acid catalyst for Friedel-Crafts reactions. / Prakash, G. K Surya; Yan, Ping; Török, Béla; Bucsi, I.; Tanaka, Mutsuo; Olah, George A.

In: Catalysis Letters, Vol. 85, No. 1-2, 01.2003, p. 1-6.

Research output: Contribution to journalArticle

Prakash, G. K Surya ; Yan, Ping ; Török, Béla ; Bucsi, I. ; Tanaka, Mutsuo ; Olah, George A. / Gallium(III) trifluormethanesulfonate : A water-tolerant, reusable Lewis acid catalyst for Friedel-Crafts reactions. In: Catalysis Letters. 2003 ; Vol. 85, No. 1-2. pp. 1-6.
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