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Cross Metathesis Allowing the Conversion of a Ruthenium Indenylidene Complex into Grubbs' Catalyst
Author(s) -
Dorta Reto,
Kelly Roy A.,
Nolan Steven P.
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404047
Subject(s) - ruthenium , chemistry , yield (engineering) , metathesis , catalysis , styrene , salt metathesis reaction , grubbs' catalyst , medicinal chemistry , organic chemistry , combinatorial chemistry , polymerization , copolymer , materials science , polymer , metallurgy
The active metathesis catalyst (PCy 3 ) 2 Cl 2 Ru(3‐phenylinden‐1‐ylidene) ( 4 ) was obtained in high yield using a simple one‐pot procedure. The initial reaction of RuCl 2 (PPh 3 ) 3 with 1,1‐diphenyl‐2‐propyn‐1‐ol gave (PPh 3 ) 2 Cl 2 Ru(3‐phenylinden‐1‐ylidene) ( 6 ). In situ exchange of PPh 3 with PCy 3 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, (PCy 3 ) 2 Cl 2 RuC(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.