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Sigma-Aldrich

SPhos

95%

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Synonym(s):
2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos
Empirical Formula (Hill Notation):
C26H35O2P
CAS Number:
657408-07-6
Molecular Weight:
410.53
MDL number:
MFCD05861611
UNSPSC Code:
12352200
NACRES:
NA.22

Assay

95%

form

powder or crystals

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
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: catalyst
reaction type: Cross Couplings
reagent type: ligand

mp

164-166 °C (lit.)
165.5 °C

functional group

phosphine

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.

Legal Information

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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)
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)
Pd-catalyzed Suzuki?Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
Altman, Ryan A., and Stephen L. Buchwald
Nature Protocols, 2.12 (2007)
Synthesis and Suzuki-Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides.
Molander GA and Shin I.
Organic Letters, 13(15), 3956-3959 (2011)
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