Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 15, Pages 5852-5858Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo800726u
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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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