638064

Sigma-Aldrich

XPhos

greener alternative

98%

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

Re-engineered,

SMILES string

CC(C)c1cc(C(C)C)c(c(c1)C(C)C)-c2ccccc2P(C3CCCCC3)C4CCCCC4

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

General description

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

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

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors,
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.
Ligand for increased scope of Pd-catalyzed amination and amidation via arene sulfonates, aryl halides.

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Tetrahedron Letters, 47, 5143-5143 (2006)
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...
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)
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...
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)
Articles
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.
Read More
Buchwald Phosphine Ligands
Read More
TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.
Read More
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
Read More

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