Crabtree's Catalyst
Title: Crabtree's Catalyst
CAS Registry Number: 64536-78-3
CAS Name: [(1,2,5,6-h)-1,5-Cyclooctadiene](pyridine)(tricyclohexylphosphine)iridium(1+) hexafluorophosphate(1-)
Additional Names: Felkin-Crabtree catalyst
Molecular Formula: C31H50IrNP.F6P
Molecular Weight: 804.89
Percent Composition: C 46.26%, H 6.26%, Ir 23.88%, N 1.74%, P 7.70%, F 14.16%
Literature References: Stereoselective organoiridium based catalyst used primarily for hydrogenation of the general formula [Ir(cod)L(py)]metal complex where cod is 1,5-cyclooctadiene, L is tertiary phosphine, py is pyridine. Prepn: R. H. Crabtree, G. E. Morris, J. Organomet. Chem. 135, 395 (1977); R. H. Crabtree et al., ibid. 141, 205 (1977); R. H. Crabtree, S. M. Morehouse, Inorg. Synth. 24, 173 (1986). Hydrogenation study: J. W. Suggs et al., Tetrahedron Lett. 22, 303 (1981); directing effects: J. M. Brown, S. A. Hall, Tetrahedron 41, 4639 (1985); R. H. Crabtree, M. W. Davis, J. Org. Chem. 51, 2655 (1986). Structure: M. S. Abbassioun et al., Acta Crystallogr. C45, 331 (1989). Synthetic applications: M. Weck et al., J. Org. Chem. 64, 5463 (1999); J. M. Bueno et al., Tetrahedron Lett. 41, 4379 (2000).
Properties: Orange crystalline solid. d 1.67 g/cm3. Air stable. Sol in CH2Cl2, CHCl3 and Me2CO. Insol in alcohols, water, benzene, diethyl ether and hexane.
Density: d 1.67 g/cm3
 
Derivative Type: Tetrafluoroborate
CAS Registry Number: 80409-82-1
Molecular Formula: C31H50IrNP.BF4
Molecular Weight: 746.73
Percent Composition: C 49.86%, H 6.75%, Ir 25.74%, N 1.88%, P 4.15%, B 1.45%, F 10.18%
 
Use: Catalyst for selective reduction of hindered carbon-carbon double bonds.

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