SPhos

SPhos
	source ↗
Names
	Preferred IUPAC name Dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)phosphane
	Other names SPhos
Identifiers
CAS Number	657408-07-6 Y;
3D model (JSmol)	Interactive image;
ChemSpider	9444883 N;
ECHA InfoCard	100.122.873
PubChem CID	11269872;
UNII	XI1MQ32186 Y;
CompTox Dashboard (EPA)	DTXSID90460730 ;
	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;
	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	soluble in 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 YN ?) Infobox references

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

References

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.
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.

[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.

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See also

References