XPhos

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XPhos
IUPAC name

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

Other names

XPhos

Identifiers
CAS number 564483-18-7 YesY
PubChem 11155794
ChemSpider 9330902 N
Jmol-3D images Image 1
Properties
Molecular formula C33H49P
Molar mass 476.72
Appearance colorless solid
Melting point 187-190 °C
Solubility in water organic solvents
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references
Not to be confused with Xantphos.

XPhos is an organophosphorus compound derived from 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.[1] The ligand has convenient handling characteristics since it is air-stable.[2]

Structure

  • One view of the molecule's structure.

  • Another view of the molecule's structure.

See also

References

  1. ↑ Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. (2003). "Expanding Pd-Catalyzed C-N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions". J. Am. Chem. Soc. 125 (22): 6653–6655. doi:10.1021/ja035483w. PMID 12769573. 
  2. ↑ Altman, R.A.; Fors, B.P.; Buchwald, S.L. (2007). "Pd-Catalyzed Amination Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands". Nature Protocols 2 (11): 2881–2887. doi:10.1038/nprot.2007.414. PMID 18007623. 
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