Stryker's reagent

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CASNo=33636-93-0
PubChem=12181933
SMILES=C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3. [CuH] . [CuH] . [CuH] . [CuH] . [CuH] . [CuH]
Section2=Chembox Properties
Formula=C₁₀₈H₉₆Cu₆P₆
MolarMass=1961.036406
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Section3=Chembox Hazards
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Stryker's reagent ( [(PPh₃)CuH] ₆ [cite journal | title = Selective Hydride-mediated conjugate reduction of α,β-unsaturated Carbonyl Compounds Using [(Ph₃P)CuH] ₆ | author = Mahoney, W.S.; Brestensky, D.M.; Stryker, J.M. | journal = J. Am. Chem. Soc. | year = 1988 | volume = 110 | pages = 291-293 | doi = 10.1021/ja00209a048] , also known as the Osborn complex, is a hexameric copper hydride ligated with triphenylphosphine. [cite journal | title = Preparation and Crystallographic Characterization of a Hexameric Triphenylphosphinecopper Hydride Cluster | author = Bezman, S. A.; Churchill, M. R.; Osborn, J. A.; Wormald, J. | journal = J. Am. Chem. Soc. | year = 1971 | volume =93 | pages = 2063-2065 | doi = 10.1021/ja00737a045] It is a brick red crystalline solid that is very sensitive to air. Stryker's reagent is a mild hydride source and is used in homogeneous catalysis of conjugate reduction reactions of various compounds (enones, enoates, etc).

Preparation and Stability

Stryker's reagent is prepared from copper(I) "tert"-butoxide, generated in situ from copper(I) chloride and sodium "tert"-butoxide, and pressurized hydrogen. It can be directly prepared from copper(II) salts as well. [cite journal | title = Direct synthesis of Stryker's reagent from Cu(II) salt | author = Lee, D. W.; Yun, J. | journal = Tetrahedron Lett. | year = 2005 | volume = 46 | pages = 2037-2039 | doi = 10.1016/j.tetlet.2005.01.127] If stored under an inert atmosphere (e.g. argon, nitrogen) it has indefinite shelf life. Brief exposure to the oxygen does not destroy its activity significantly, although solvents used with Stryker's reagent should be rigorously degassed. [e-EROS Encyclopedia of Reagents for Organic Synthesis http://www.mrw.interscience.wiley.com/eros/articles/rh011m/sect0-fs.html ]

Modifications to Stryker's reagent

Ligand modified versions of Stryker's reagent have been reported. These modifications claim to be more reactive and/or more stable in the atmosphere.

References