Bismuth(III) Trifluoromethanesulfonate: A Chameleon Catalyst for the Friedel–Crafts Acylation

Autor:	Christophe Le Roux, Jacques Dubac, Jean-Roger Desmurs, Sigrid Repichet
Rok vydání:	1998
Předmět:	Organic Chemistry Toluene Catalysis chemistry.chemical_compound chemistry Chlorobenzene Reagent Polymer chemistry Organic chemistry Lewis acids and bases Physical and Theoretical Chemistry Benzene Friedel–Crafts reaction Trifluoromethanesulfonate
Zdroj:	European Journal of Organic Chemistry. 1998:2743-2746
ISSN:	1099-0690 1434-193X
Popis:	A mechanism for acylations catalyzed by bismuth(III) triflate (1) is proposed in the case of the benzoylation of benzene, toluene, and chlorobenzene. With Bz2O as a reagent, 1 acts as a Lewis acid and allows the benzoylation of toluene. It is almost completely recovered after the reaction. With BzCl, 1 promotes an exchange reaction which generates BzOTf, which is the active species of the benzoylation. In this latter case, the reaction leads to the formation of TfOH which finally reacts with BiCl3 to partially regenerate 1. The power of the Bz2O/1 system is less than that of BzCl/1, which allows not only the benzoylation of toluene but also that of benzene and deactivated chlorobenzene. The activity of 1 is much higher than that of other metallic triflates previously reported, and is comparable with that of TfOH, however it also has the advantage that the triflate moieties are more easily recoverable.
Databáze:	OpenAIRE
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