SPhos

SPhos
IUPAC name 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
Other names SPhos
Identifiers
CAS number	657408-07-6 Y
PubChem	11269872
ChemSpider	9444883 N
Jmol-3D images	Image 1
SMILES COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC
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 N Key: VNFWTIYUKDMAOP-UHFFFAOYSA-N 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
Properties
Molecular formula	C26H35O2P
Molar mass	410.53 g/mol
Appearance	colorless solid
Melting point	164-166 °C
Solubility in water	organic solvents
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.