564483-18-7

Raw materials And Preparation Products

Hazard Information

Chemical Properties

White crystalline powder

Uses

Exceptional ligands for Pd-catalyzed amination and amidation of aryl sulfonates. XPHOS is used as a regent in the synthesis of novel [1,2,4]triazolo[4,3-a]pyrazine derivatives as potential selective c-met inhibitors with improved pharmacokinetic properties.

Uses

suzuki reaction

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.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

Synthesis

21524-34-5

16523-54-9

583-53-9

564483-18-7

Under nitrogen protection, 200 mL of tetrahydrofuran (THF) and 31 g of 2-bromo-1,3,5-triisopropylbenzene were added to a 1 L three-necked flask. The reaction mixture was cooled to 0 °C and 46 mL of a 2.5 M hexane solution of n-butyllithium was slowly added dropwise. After the dropwise addition was completed, the reaction continued to be stirred at 0 °C for 1 hour. Subsequently, 24.6 g of 1,2-dibromobenzene was slowly added dropwise at the same temperature. After completion of the dropwise addition, the reaction was continued at 0°C for 1 hour. Next, 42 mL of 2.5 M hexane solution of n-butyllithium was added dropwise to the reaction mixture at 0 °C. After the dropwise addition was completed, the reaction was continued with stirring at 0 °C for 1 hour. Then, 26.7 g of dicyclohexylphosphonium chloride was slowly added dropwise and the reaction mixture was allowed to warm up to room temperature naturally and the reaction was continued to be stirred for 2 hours. Upon completion of the reaction, 200 mL of saturated aqueous ammonium chloride solution was slowly added dropwise to quench the reaction under the cooling of an ice bath. After performing phase separation, the organic phase was concentrated and crystallized by adding methanol. The solid was collected by filtration to afford 44.5 g of a white crystalline product of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl in 89% yield.

References

[1] Patent: CN105273006, 2016, A. Location in patent: Paragraph 0069; 0070

Questions And Answer

• Reaction

  1.  Exceptional ligands for Pd-catalyzed amination and amidation of aryl sulfonates.
  2.  Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling reaction and carbonyl enolate coupling.
  3.  Ligand used for the chemoselective amination of aryl chlorides.
  4.  Ligand used for the Pd-catalyzed borylation of aryl chlorides, for the formation of trifluoroborates.
  5.  Ligand used for the Pd-catalyzed amination of vinyl halides and triflates.
  6.  Ligand used for the Pd-catalyzed three-component synthesis of indoles.
  7.  Ligand used for the Pt-catalyzed regioselective hydrosilylation of functionalized terminal arylalkynes.
  8.  Ligand used for the Pd-catalyzed synthesis of carbazoles.
  9.  Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling of aryl chloride and NHC-boranes.
  10.  Ligand used for the direct arylation of picoline N-oxide.
  11.  Ligand used for the Negishi coupling of 2-heterocyclic organozinc reagents.
  12.  Catalyst for a phosphine-catalyzed Heine reaction.
  13.  Ligand used for the palladium-catalyzed oxidative coupling of indoles and heteroarenes.
  14.  Ligand used for the silver-catalyzed hydrogenation of aldehydes.
  15.  Ligand used for the palladium-catalyzed cyanation of heterycyclic halides.
  
  
  
  ;

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products