SPhos

SPhos

Names
IUPAC name 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
Other names SPhos
Identifiers
CAS Number	657408-07-6
3D model (Jmol)	Interactive image
ChemSpider	9444883
ECHA InfoCard	100.122.873
PubChem	11269872
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

SPhos is an organophosphorus compound 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]

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.