XPhos

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IUPACName = 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
OtherNames = XPhos
Section1 = Chembox Identifiers
CASNo = 564483-18-7
PubChem = 24882906
SMILES =
Section2 = Chembox Properties
Formula = C₃₃H₄₉P
MolarMass = 476.72
Appearance = colorless solid
Density =
MeltingPt = 187-190 °C
BoilingPt =
Solubility = organic solvents
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

XPhos is an organophosphorus compound derived from the biphenyl. Its palladium complexes exhibit high activity for Buchwald-Hartwig amination reactions involving aryl chlorides and aryl tosylates. Both palladium and copper complexes of the compound exhibit high activity for the coupling of aryl halides and aryl tosylates with various amides. [cite journal | author = Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. | title = Expanding Pd-Catalyzed C-N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions | year = 2003 | journal = J. Am. Chem. Soc. | volume = 125 | issue = | pages = 6653-6655 | doi = 10.1021/ja035483w] The ligand has convenient handling characteristics since it is air-stable. [cite journal | author = Altman, R.A.; Fors, B.P.; Buchwald, S.L. | title = Pd-Catalyzed Amination Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands | year = 2007 | journal = Nature Protocols | volume = 2 | issue = | pages = 2881-2887 | doi = 10.1038/nprot.2007.414]

tructure

ee also

* SPhos
* Buchwald-Hartwig reaction

References