Merck
CN
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638064

Sigma-Aldrich

XPhos

greener alternative

98%

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Synonym(s):
2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
Empirical Formula (Hill Notation):
C33H49P
CAS Number:
Molecular Weight:
476.72
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

reaction suitability

reaction type: Cross Couplings
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

greener alternative product score

old score: 2
new score: 1
Find out more about DOZN™ Scoring

greener alternative product characteristics

Waste Prevention
Atom Economy
Use of Renewable Feedstocks
Catalysis
Learn more about the Principles of Green Chemistry.

mp

187-190 °C (lit.)

functional group

phosphine

greener alternative category

SMILES string

CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2

InChI

1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3

InChI key

UGOMMVLRQDMAQQ-UHFFFAOYSA-N

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663131638080638072
XPhos 98%

Sigma-Aldrich

638064

XPhos

RuPhos 98%

Sigma-Aldrich

663131

RuPhos

tBuXPhos 98%

Sigma-Aldrich

638080

tBuXPhos

SPhos 98%

Sigma-Aldrich

638072

SPhos

reaction suitability

reaction type: Cross Couplings, 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

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Sonogashira Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Carboxylations, reagent type: ligand
reaction type: Decarboxylations

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

mp

187-190 °C (lit.)

mp

123-126 °C

mp

148-151 °C (lit.)

mp

164-166 °C (lit.)

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

300

Quality Level

-

Quality Level

-

Quality Level

-

greener alternative product score

old score: 2
new score: 1
Find out more about DOZN™ Scoring

greener alternative product score

old score: 3
new score: 1
Find out more about DOZN™ Scoring

greener alternative product score

old score: 12
new score: 1
Find out more about DOZN™ Scoring

greener alternative product score

old score: 10
new score: 1
Find out more about DOZN™ Scoring

General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Atom Economy”, “Use of Renewable Feedstock” and “Enhanced Catalytic Activity”. Click here to view its DOZN scorecard.
We are 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 catalytic efficiency. Click here for more information.
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.

Application

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.

For small scale and high throughput uses, product is also available as ChemBeads (928364)

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

Legal Information

Usage subject to US Patent 7,223,879
Usage subject to US Patents 6307087 and 6395916.

related product

Product No.
Description
Pricing

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Yanxing Jia et al.
The Journal of organic chemistry, 71(20), 7826-7834 (2006-09-26)
One-pot synthesis of indoles by a palladium-catalyzed annulation of ortho-haloanilines and aldehydes has been developed. Coupling of ortho-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85 degrees C], whereas X-Phos is found to be the ligand
Palladium-Catalyzed Stille Cross-Coupling Reaction of Aryl Chlorides using a Pre-Milled Palladium Acetate and XPhos Catalyst System.
Advanced Synthesis & Catalysis, 350(7-8), 957-961 (2008)
Peter D Johnson et al.
The Journal of organic chemistry, 71(20), 7899-7902 (2006-09-26)
Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo- and iodovindolines were prepared in high yield by the reaction of vindoline with N-bromosuccinimide or N-iodosuccinimide, respectively. The study
Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized ?-(E)-vinylsilanes from terminal alkynes.
Hamze A, et al.
Journal of Organometallic Chemistry, 693(16), 2789-2797 (2008)
Tetrahedron Letters, 47, 5143-5143 (2006)

Articles

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under mild room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Protocols

Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, may be used in water at room temperature for Buchwald-Hartwig Amination, Suzuki-Miyaura reactions, Heck reactions, Sonogashira reactions, Negishi reactions, and olefin metathesis.

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