Jump to content

SPhos

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Fswitzer4 (talk | contribs) at 14:43, 25 June 2020 (Added FDA UNII). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

SPhos
Names
IUPAC name
2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
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 ☒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
  • 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)
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

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.