Crabtree's catalyst

Crabtree's catalyst is an organoiridium compound with the formula [C8H12IrP(C6H11)3C5H5N]PF6. It is a homogeneous catalyst for hydrogenation and hydrogen-transfer reactions, developed by Robert H. Crabtree. This air stable orange solid is commercially available and known for its directed hydrogenation to give trans stereoselectivity with respective of directing group.

Crabtree's catalyst
Names
IUPAC name
(SP-4)-(η2,η2-Cycloocta-1,5-diene)(pyridine)(tricyclohexylphosphane)iridium(1+) hexafluoridophosphate(1−)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.161
PubChem CID
UNII
  • InChI=1S/C18H33P.C8H12.C5H5N.F6P.Ir/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-6-8-7-5-3-1;1-2-4-6-5-3-1;1-7(2,3,4,5)6;/h16-18H,1-15H2;1-2,7-8H,3-6H2;1-5H;;/q;;;-1;+1/b;2-1-,8-7-;;; N
    Key: UJXHUUQZACSUOG-KJWGIZLLSA-N N
  • InChI=1/C18H33P.C8H12.C5H5N.F6P.Ir/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-6-8-7-5-3-1;1-2-4-6-5-3-1;1-7(2,3,4,5)6;/h16-18H,1-15H2;1-2,7-8H,3-6H2;1-5H;;/q;;;-1;+1/b;2-1-,8-7-;;;
    Key: UJXHUUQZACSUOG-KJWGIZLLBW
SMILES
  • c1ccncc1.C1CCC(CC1)P(C2CCCCC2)C3CCCCC3.C1/C=C\CC/C=C\C1.F[P-](F)(F)(F)(F)F.[Ir+]
Properties
C31H50F6IrNP2
Molar mass 804.9026 g/mol
Appearance Yellow microcrystals
Melting point 150 °C (302 °F; 423 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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