SPhos

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title: "SPhos" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tertiary-phosphines"] topic_path: "general/tertiary-phosphines" source: "https://en.wikipedia.org/wiki/SPhos" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424977941 | ImageFile = SPhos.svg | ImageSize = | ImageFile1 = | ImageSize1 = | PIN = Dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)phosphane | OtherNames = SPhos |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 657408-07-6 | UNII_Ref = | UNII = XI1MQ32186 | PubChem = 11269872 | ChemSpiderID_Ref = | ChemSpiderID = 9444883 | SMILES = COc1cccc(c1c2ccccc2P(C3CCCCC3)C4CCCCC4)OC | 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 | InChIKey = VNFWTIYUKDMAOP-UHFFFAOYAH | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = VNFWTIYUKDMAOP-UHFFFAOYSA-N |Section2={{Chembox Properties | Formula = C26H35O2P | MolarMass = 410.53 g/mol | Appearance = colorless solid | Density = | MeltingPtC = 164 to 166 | MeltingPt_notes = | BoilingPt = | SolubleOther = soluble in organic solvents |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

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.

References

References

  1. (2005). "New Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure". [[J. Am. Chem. Soc.]].
  2. (2007). "Pd-Catalyzed Suzuki-Miyaura Reactions of Aryl Halides Using Bulky Biarylmonophosphine Ligands". [[Nature Protocols]].

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tertiary-phosphines