SPhos

SPhos is a phosphine ligand derived from biphenyl. Its palladium complexes exhibit high activity for Suzuki coupling reactions involving aryl chlorides, which are unreactive with palladium complexes of most other phosphine ligands.[1] The ligand has convenient handling characteristics since it is air-stable.[2]

SPhos

Names
IUPAC name 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
Other names SPhos
Identifiers
CAS Number	657408-07-6
3D model (JSmol)	Interactive image
ChemSpider	9444883
ECHA InfoCard	100.122.873
PubChem CID	11269872
UNII	XI1MQ32186
CompTox Dashboard (EPA)	DTXSID90460730
InChI InChI=1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3 Key: VNFWTIYUKDMAOP-UHFFFAOYSA-N InChI=1/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3 Key: VNFWTIYUKDMAOP-UHFFFAOYAH
SMILES COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC
Properties
Chemical formula	C26H35O2P
Molar mass	410.53 g/mol
Appearance	colorless solid
Melting point	164 to 166 °C (327 to 331 °F; 437 to 439 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).
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Infobox references

See also

• XPhos
• CPhos
• Suzuki reaction

References

1. Barder, T.E.; Walker, S.D.; Martinelli, J.R.; Buchwald, S. L. (2005). "New Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure". J. Am. Chem. Soc. 127 (13): 4685–4696. doi:10.1021/ja042491j. PMID 15796535.
2. Altman, R.A.; Buchwald, S.L. (2007). "Pd-Catalyzed Suzuki-Miyaura Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands". Nature Protocols. 2 (12): 3115–3121. doi:10.1038/nprot.2007.411. PMID 18079711.