XPhos

XPhos
Names
	Preferred IUPAC name Dicyclohexyl[2′,4′,6′-tris(propan-2-yl)[1,1′-biphenyl]-2-yl]phosphane
	Other names XPhos
Identifiers
CAS Number	564483-18-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	9330902 ;
ECHA InfoCard	100.123.428
PubChem CID	11155794;
UNII	R271FU23T8 ;
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 a phosphine ligand 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. It is also an efficient ligand for several commonly used C–C bond-forming cross-coupling reactions, including the Negishi, Suzuki, and the copper-free Sonogashira coupling reactions. It is especially efficient and general when employed as a (2-aminobiphenyl)-cyclometalated palladium mesylate precatalyst complex (Buchwald's third generation precatalyst system), XPhos-G3-Pd, which is commercially available and stable to bench storage. The ligand itself also has convenient handling characteristics as a crystalline, air-stable solid.