Ruthenium/TFA-catalyzed coupling of activated secondary propargylic alcohols with cyclic 1,3-diones: furan versus pyran ring formation |
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Authors: | Cadierno Victorio Díez Josefina Gimeno José Nebra Noel |
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Affiliation: | Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica Enrique Moles (Unidad Asociada al CSIC), Facultad de Química, Universidad de Oviedo, E-33071 Oviedo, Spain. vcm@uniovi.es |
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Abstract: | A catalytic system consisting of the 16-electron allyl-ruthenium(II) complex [Ru(eta(3)-2-C3H4Me)(CO)(dppf)][SbF6] (dppf = 1,1'-bis(diphenylphosphino)ferrocene) and trifluoroacetic acid (TFA) has been used to promote the coupling between secondary propargylic alcohols and cyclic 1,3-diketones. The nature of the resulting products was found to be dependent on the ring size of the dicarbonyl compound employed. Thus, whereas 6,7-dihydro-5H-benzofuran-4-ones have been selectively obtained starting from 1,3-cyclohexanediones, via furan-ring formation, the use of 1,3-cyclopentanedione leads instead to 6,7-dihydro-4H-cyclopenta[b]pyran-5-ones via a pyran-ring formation process. |
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