638072

Sigma-Aldrich

SPhos

greener alternative

98%

Synonym(s):
S Phos, 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, SPhos
Empirical Formula (Hill Notation):
C26H35O2P
CAS Number:
Molecular Weight:
410.53
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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

greener alternative product score

old score: 10
new score: 1
Find out more about DOZN™ Scoring.

greener alternative product characteristics

Waste Prevention
Less Hazardous Chemical Syntheses
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

mp

164-166 °C (lit.)

functional group

phosphine

greener alternative category

Re-engineered

SMILES string

COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

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

InChI key

VNFWTIYUKDMAOP-UHFFFAOYSA-N

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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.

Application

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.

Packaging

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

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

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)
Articles
Buchwald Phosphine Ligands
Read More
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
Read More

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