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638064 Sigma-Aldrich

XPhos Green Alternative

97%

Synonym: 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

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Properties

Related Categories 12 Principles Aligned Products, Buchwald Ligands, Buchwald Ligands and Complexes, Catalysis, Catalysis and Inorganic Chemistry,
InChI Key   UGOMMVLRQDMAQQ-UHFFFAOYSA-N
assay   97%
greener alternative product characteristics   Catalysis
Learn more about the Principles of Green Chemistry.
mp   187-190 °C (lit.)
reaction suitability   reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reagent type: ligand
reaction type: C-C Bond Formation
  reagent type: ligand
reaction type: Heck Reaction
  reagent type: ligand
reaction type: Hiyama Coupling
  reagent type: ligand
reaction type: Negishi Coupling
  reagent type: ligand
reaction type: Sonogashira Coupling
  reagent type: ligand
reaction type: Stille Coupling
  reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Description

Application

Ligand for increased scope of Pd-catalyzed amination and amidation via arene sulfonates, aryl halides.

Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.
Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd. Synthesis of regioregular polythiophenes.

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

XPhos may be used as a ligand in the following reactions:
• Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.
• Along with pre-milled palladium(II) acetate as a pre-catalyst for the Stille cross-coupling of aryl chlorides with tributylarylstannanes to form the corresponding biaryl compounds.
• Along with platinum chloride to catalyze the hydrosilylation of terminal arylalkynes with silanes to form functionalized β-(E)-vinylsilanes.

Packaging

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

Legal Information

Usage subject to US Patent 7,223,879

Usage subject to US Patents 6307087 and 6395916.

General description

Sigma Life Science is committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here.

XPhos [2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable electron-rich biaryl monophosphine ligand2 developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

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

Catalytic Direct Cross-Coupling of Organolithium Compounds with Aryl Chlorides

Complex, hindered biaryls have been prepared at temperatures ranging from 1�C to room temperature, or with gentle heating. The Pd-PEPPSI-IPent catalyst nicely couples starting materials containing ac...
Keywords: Chromatography, Flash chromatography

Copper-Free Sonogashira Coupling of Cyclopropyl Iodides with Terminal Alkynes

An efficient palladium-catalyzed cyanation of aryl chlorides is established. In the presence of a highly effective Pd/CM-phos catalyst, cyanation of aryl chlorides proceeds at 71 �C in general, which...
Keywords: Catalysis, Chromatography, Column chromatography, Gas chromatography, Ligands, Nuclear magnetic resonance spectroscopy

Pd-Catalyzed Cross-Coupling Reactions

A variety of widely used palladium-catalyzed cross-coupling reactions can now be run under mild room temperature conditions in water with TPGS- 750-M, using a variety of commercially available pallad...
Troy Ryba
ChemFiles Volume 11 Article 1
Keywords: Aminations, Catalysis, Coupling reactions, Cross couplings, Ligands

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

Protocols

Boxed reaction: Sonogashira Coupling in Lipshutz Surfactant

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.
Keywords: Chromatography, Coupling reactions, Flash chromatography, Sonogashira Coupling

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions

TPGS-750-M, DL-α-Tocopherol methoxypolyethylene glycol succinate, is a designer surfactant composed of a lipophilic α-tocopherol moiety and a hydrophilic PEG-750-M chain, joined by an inexpensive suc...
Keywords: Aminations, Buchwald-Hartwig amination, Catalysis, Chromatography, Coupling reactions, Cross couplings, Environmental, Evaporation, Flash chromatography, Heck Reaction, Ligands, Metathesis, Olefin metathesis

Sonogashira Kit

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.
Keywords: Chromatography, Column chromatography, Gas chromatography, High performance liquid chromatography, Ligands, Thin layer chromatography

Sonogashira Reaction in Water at Room Temperature using TPGS-750-M

TPGS-750-M, DL-α-Tocopherol methoxypolyethylene glycol succinate, is a designer surfactant composed of a lipophilic α-tocopherol moiety and a hydrophilic PEG-750-M chain, joined by an inexpensive suc...
Keywords: Catalysis, Chromatography, Coupling reactions, Cross couplings, Environmental, Flash chromatography

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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