XPhos

XPhos

Names
IUPAC name 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
Other names XPhos
Identifiers
CAS Registry Number	564483-18-7 Y
ChemSpider	9330902 N
InChI InChI=1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3 N Key: UGOMMVLRQDMAQQ-UHFFFAOYSA-N N InChI=1/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3 Key: UGOMMVLRQDMAQQ-UHFFFAOYAR
Jmol-3D images	Image
PubChem	11155794
SMILES P(c2ccccc2c1c(cc(cc1C(C)C)C(C)C)C(C)C)(C3CCCCC3)C4CCCCC4
Properties
Chemical formula	C33H49P
Molar mass	476.72
Appearance	colorless solid
Melting point	187 to 190 °C (369 to 374 °F; 460 to 463 K)
Solubility in water	organic solvents
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

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

• SPhos
• CPhos
• Buchwald-Hartwig reaction

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.