Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 1-2, Pages 243-254Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600461
Keywords
alkene metathesis; fluorous; Grubbs' catalyst; phase transfer; phosphines; recycling
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Reactions of the bis(pyridine) complex (H(2)IMes)(Py)(2)(Cl)(2)Ru(=CHPh), (H(2)IMes = 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene) and the highly fluorophilic phosphines [R-fn(CH2)(m)](3)P [1; m/n = a, 2/6; b, 2/8; c, 2/10; d, 3/8; R-fn = CF3(CF2)(n-1)] give (H(2)IMes)([R-fn(CH2)(m)](3)P}(Cl)(2)Ru(=CHPh) (4a-d, 64-78%), which are analogues of Grubbs' second generation alkene metathesis catalyst. Complexes 4a,b are effective catalysts for conversions of 1,6-dienes to cyclopentenes under monophasic and bi-phasic conditions in CH2Cl2 and CH2Cl2/fluorous solvent mixtures. The latter generally exhibit rate accelerations, which are believed to arise from phase transfer of the dissociated fluorous phosphine, allowing the substrate to better compete for the fourteen valence-electron intermediate. Only modest effects are observed when Grubbs' second generation catalyst is similarly reacted. The most fluorophilic catalyst, 4c, can be recycled by extracting the reaction mixtures with perfluoro(methylcyclohexane).
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