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638072 Sigma-Aldrich

SPhos

Green Alternative

97%

Synonym: 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos, SPhos

  • CAS Number 657408-07-6

  • Empirical Formula (Hill Notation) C26H35O2P

  • Molecular Weight 410.53

  •  MDL number MFCD05861611

  •  PubChem Substance ID 24882907

  •  NACRES NA.22

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Properties

Related Categories Buchwald Ligands, Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis, Catalysis and Inorganic Chemistry,
assay   97%
greener alternative product score   old score: 10
new score: 1
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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
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
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

Description

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

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Buchwald Phosphine Ligands - Technical Article

Over the past several years, the Buchwald group has developed a series of bulky electron-rich phosphines that have garnered much attention for their ability to effect various C–C, C–N, and C–O bond f...
Keywords: Aldrichimica Acta, Arylations, C-X bond formation, Catalysis, Chemfiles, Coupling reactions, Ligands, Methods, Type

Buchwald Phosphine Ligands

Sigma-Aldrich is pleased to offer an array of phosphines for C-C, C-N, and C-O bond formation.
ChemFiles Volume 4 Article 2
Keywords: Amidations, Aminations, Applications, Arylations, Catalysis, Coupling reactions, Cross couplings, Ligands, Organic synthesis, Sonogashira Coupling, Suzuki-Miyaura coupling

Related Content

Buchwald Phosphine Ligands - For C-C, C-N, and C-O Bond Formation

For C-C, C-N, and C-O Bond Formation: Over the past several years, the Buchwald group has developed a series of bulky electron-rich phosphines that have garnered much attention for their ability to e...
Keywords: Aldrichimica Acta, Arylations, Catalysis, Chemfiles, Coupling reactions, Ligands, Methods, Type

Buchwald Precatalysts and Ligand Guide

Dialkylbiaryl phospine ligands, and the precatalysts derived from them, are commonly referred to as Buchwald Precatalysts and Ligands. These reagents have developed into a highly valuable class of co...
Keywords: Catalysis, Ligands

Peer-Reviewed Papers
15

References

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