XPhos

XPhos
Names
	IUPAC name 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
	Other names XPhos
Identifiers
CAS Number	564483-18-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	9330902 ;
ECHA InfoCard	100.123.428
PubChem CID	11155794;
CompTox Dashboard (EPA)	DTXSID50457126 ;
	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 Key: UGOMMVLRQDMAQQ-UHFFFAOYSA-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;
	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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

References

^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1]

[2]

Structure

See also

References