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S Phos, 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, SPhos
Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:
MDL number:
PubChem Substance ID:

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reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Kumada Coupling

reagent type: ligand
reaction type: Negishi Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

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old score: 10
new score: 1
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Waste Prevention
Less Hazardous Chemical Syntheses
Inherently Safer Chemistry for Accident Prevention
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164-166 °C (lit.)

functional group


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General description

SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.


SPhos may be used as a ligand in the following processes:
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
  • Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation.
Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.


1, 5, 25, 100, 500 g in glass bottle

Legal Information

Usage subject to Patents: US 6307087; EP 1097158; JP 5758844; CA 2336691

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves


NONH for all modes of transport

WGK Germany


Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Use of the SPhos Ligand to Suppress Racemization in Arylpinacolboronate Ester Suzuki Couplings Involving ?-Amino Acids. Synthesis of Biaryl Derivatives of 4-Hydroxyphenylglycine, Tyrosine, and Tryptophan
Prieto, Monica, et al.
The Journal of Organic Chemistry, 74.23, 9202-9205 (2009)
Highly diastereoselective arylations of substituted piperidines
Seel, Stephanie, et al.
Journal of the American Chemical Society, 133.13, 4774-4777 (2011)
Efficient synthesis of functionalized dibenzofurans by domino `twofold Heck/6?-electrocyclization?reactions of 2, 3-di-and 2, 3, 5-tribromobenzofuran
Hussain, Munawar, Nguyen Thai Hung, and Peter Langer
Tetrahedron Letters, 50.27, 3929-3932 (2009)
Synthesis of 1, 5-disubstituted tetrazoles via Suzuki?Miyaura cross-coupling of 5-chloro-1-phenyltetrazole
Tang, Qing, and Ryan Gianatassio
Tetrahedron Letters, 51.27, 3473-3476 (2010)
What makes for a good catalytic cycle? A theoretical study of the SPhos ligand in the Suzuki?Miyaura reaction
Kozuch, Sebastian, and Jan ML Martin
Chemical Communications (Cambridge, England), 47.17, 4935-4937 (2011)
Buchwald Phosphine Ligands
Read More
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
Read More

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