Isomerization of alkyl allyl and allyl silyl ethers catalyzed by ruthenium complexes

The results of double-bond migration in alkyl allyl and allyl silyl ethers catalyzed by ruthenium complexes [RuClH(CO)(PPh3)3] and in situ forming catalytic system {[RuCl2(cod)]x} with hydride and a phosphine) are presented. The conversion of allyl to 1-propenyl ethers is quantitative. The mechanism of double-bond migration has been investigated on deuterated reagents. It has been proved that the reaction is consistent with hydride mechanism, which encompasses addition and elimination of RuH and intermolecular exchange of hydrogen. We are presenting the first literature description of the direct recycling investigation of ruthenium catalyst for double-bond migration. The recycling has been investigated on model reaction of isomerization of 1,4-diallyloxybutane with [RuClH(CO)(PPh3)3]. It has been shown that fivefold recycle of the catalyst was successful. In the recycling investigation it has been found that the highest activity loss occurred after first use of the catalyst.

Graphical abstractDouble-bond migration in alkyl allyl and allyl silyl ethers was catalysed by ruthnium complexes. Mechanism of the reaction and catalyst recycling have been studied. Figure optionsDownload full-size imageDownload as PowerPoint slide