SPhos

SPhos
Names
Preferred IUPAC name
Dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)phosphane
Other names
SPhos
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.122.873 Edit this at Wikidata
UNII
  • 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 X markN
    Key: VNFWTIYUKDMAOP-UHFFFAOYSA-N X markN
  • 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
  • COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC
Properties
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 soluble in 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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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. The ligand has convenient handling characteristics since it is air-stable.

See also

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. S2CID 11069335.