XPhos

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XPhos
XPhos.png
Names
IUPAC name
2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
Other names
XPhos
Identifiers
564483-18-7 YesY
ChemSpider 9330902 N
Jmol-3D images Image
PubChem 11155794
Properties
C33H49P
Molar mass 476.72
Appearance colorless solid
Melting point 187 to 190 °C (369 to 374 °F; 460 to 463 K)
organic solvents
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

See also[edit]

References[edit]

  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.