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638072 Aldrich

SPhos

97%

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

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Properties

Related Categories Buchwald Ligands, Buchwald Ligands and Complexes, Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis,
InChI Key   VNFWTIYUKDMAOP-UHFFFAOYSA-N
assay   97%
mp   164-166 °C(lit.)
ligand for   Buchwald-Hartwig Cross Coupling Reaction
  Heck Reaction
  Kumada Coupling
  Negishi Coupling
  Suzuki-Miyaura Coupling

Description

Application

Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

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.

Packaging

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

Legal Information

Usage subject to US Patents 6307087 and 6395916.

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.

Price and Availability


KitAlysis - Increasing Catalysis Productivity

Cross-Coupling Guide
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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