Cross Metathesis Allowing the Conversion of a Ruthenium Indenylidene Complex into Grubbs' Catalyst

The active metathesis catalyst (PCy3)2Cl2Ru(3‐phenylinden‐1‐ylidene) (4) was obtained in high yield using a simple one‐pot procedure. The initial reaction of RuCl2(PPh3)3 with 1,1‐diphenyl‐2‐propyn‐1‐ol gave (PPh3)2Cl2Ru(3‐phenylinden‐1‐ylidene) (6). In situ exchange of PPh3 with PCy3 led to the iso...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2004-07, Vol.346 (8), p.917-920
Main Authors: Dorta, Reto, Kelly III, Roy A., Nolan, Steven P.
Format: Article
Language:English
Subjects:
cross metathesis
Grubbs' catalyst
homogeneous catalysis
metal carbenes
ruthenium
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Summary:The active metathesis catalyst (PCy3)2Cl2Ru(3‐phenylinden‐1‐ylidene) (4) was obtained in high yield using a simple one‐pot procedure. The initial reaction of RuCl2(PPh3)3 with 1,1‐diphenyl‐2‐propyn‐1‐ol gave (PPh3)2Cl2Ru(3‐phenylinden‐1‐ylidene) (6). In situ exchange of PPh3 with PCy3 led to the isolation of 4 in>90% yield. Whereas complex 6 did not show any activity in the cross metathesis reaction with styrene, reaction of compound 4 with excess styrene gave Grubbs' catalyst, (PCy3)2Cl2RuC(H)Ph (1), dichloro(phenylmethylene)bis(tricyclohexylphosphane)ruthenium(II), in nearly quantitative yield. This two‐step procedure yielded complex 1 in 88% overall yield starting from inexpensive and commercially available materials. The widely used metathesis catalyst 1 was also obtained in good yield in one single step, that is, without isolation of compound 4, making this a simple and safe synthetic route to Grubbs' catalyst.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404047