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DOI: 10.1055/s-2008-1077954
FeCl3-Catalyzed Intramolecular Hydroarylation of Alkynes
Publikationsverlauf
Publikationsdatum:
15. Juli 2008 (online)
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Abstract
The intramolecular hydroarylation of alkynes using a substoichiometric amount of FeCl3 is described. When starting from tetrasubstituted substrates, products resulting from an unexpected toluene (or xylene) elimination are isolated in good yields.
Key words
electrophilic aromatic substitutions - arylations - iron - ring closure
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References and Notes
As pointed out by a referee, the lack of reactivity in compound 2e can also be explained by some poisoning effect of the nitro group which kills the Lewis acidity of FeCl3.
11General Procedure: To a solution of alkyne (0.2 mmol) in 1,2-dichloroethane (8 mL) under nitrogen was added iron(III) chloride hexahydrate (0.02 mmol, finely ground). The mixture was then stirred at r.t. until completion of the reaction (TLC monitoring). The mixture was concentrated under vacuum and the crude material was loaded onto a silica gel column and chromatographed with heptane to give the cyclization product.