Cadierno Victorio, Díez Josefina, Gimeno José, Nebra Noel
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.
J Org Chem. 2008 Aug 1;73(15):5852-8. doi: 10.1021/jo800726u. Epub 2008 Jul 2.
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.
由16电子烯丙基钌（II）配合物[Ru(η(3)-2-C3H4Me)(CO)(dppf)][SbF6]（dppf = 1,1'-双（二苯基膦基）二茂铁）和三氟乙酸（TFA）组成的催化体系已被用于促进仲炔丙醇与环状1,3-二酮之间的偶联反应。结果发现所得产物的性质取决于所用二羰基化合物的环大小。因此，从1,3-环己二酮开始，通过呋喃环的形成可选择性地得到6,7-二氢-5H-苯并呋喃-4-酮，而使用1,3-环戊二酮则通过吡喃环的形成过程得到6,7-二氢-4H-环戊并[b]吡喃-5-酮。
