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718742 Sigma-Aldrich

BrettPhos

96%

Synonym: 2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl

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Properties

Related Categories Buchwald Ligands, Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis, Catalysis and Inorganic Chemistry,
InChI Key   WDVGNXKCFBOKDF-UHFFFAOYSA-N
assay   96%
mp   187-195 °C
reaction suitability   reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reagent type: ligand
reaction type: Fluorinations

Description

Packaging

1, 5, 25, 50 g in glass bottle

100, 500 mg in glass bottle

Application

Buchwald Phosphine Ligands for chemical Synthesis

BrettPhos is a dialkylbiaryl phosphine ligand developed by the Buchwald group. It promotes cross-coupling reactions more efficiently and exhibits improved reactivity compared to other catalytic systems.
It can be used in:
• palladium-catalyzed trifluoromethylation of aryl chlorides
• Buchwald-Hartwig amination
• synthesis of 4-aryl and alkyl substituted, N6-alkylated pyridazine-3,6-diamines via a Buchwald protocol

Features and Benefits

• White crystalline solid
• Air- and moisture-stable
• Thermally stable
• Highly efficient
• Wide functional group tolerance
• Excellent selectivity and conversion

Safety & Documentation

Safety Information

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

Articles

BrettPhos Ligand Supported Palladium-Catalyzed C-O Bond Formation through an Electronic Pathway of Reductive Elimination: Fluoroalkoxylation of Activated Aryl Halides

A Pd/N-heterocyclic carbene-based catalyst achieves the Sonogashira coupling of an array of functionalized, ?-hydrogen-containing alkyl bromides and iodides under mild conditions. By furnishing the f...
Keywords: Chromatography, Cross couplings, Flash chromatography, Ligands, Sonogashira Coupling

N-Arylation of Aryl Mesylates and Monoarylation of Primary Amines Using BrettPhos

Buchwald and coworkers recently reported the use of a catalyst system comprised of the highly efficient ligand 2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl- 1,1′-biphenyl (718742) (Br...
Josephine Nakhla
Keywords: Arylations, Chemfiles, Ligands

Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases

We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C-N cross-coupling reactions to date. Often low ca...
Keywords: Arylations, Catalysis, Coupling reactions, Cross couplings, Ligands, Pharmaceutical

Pd-Catalyzed Synthesis of Ar-SCF3 Compounds under Mild Conditions-

We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use o...
Keywords: Chromatography, Column chromatography, Coupling reactions, Supercritical fluid chromatography

Stephen Buchwald Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Stephen Buchwald Group – Professor Product Portal
Keywords: Aminations, Asymmetric catalysis, Asymmetric synthesis, Catalysis, Coupling reactions, Cross couplings, Fluorinations, Ligands, Solvents, transformation

The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides

A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were ...
Keywords: Chromatography, Flash chromatography

Related Content

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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