224311-49-3

Usage

Reaction

Useful ligand for Pd-catalyzed carbon-oxygen bond forming reactions. Ligand used selective Pd-catalyzed arylation of ammonia. Application to the synthesis of dibenzodiazepines. Ligand used for selective Pd-catalyzed silylation of aryl chlorides. Ligand used for Pd(0)-catalyzed direct dehydrative coupling of terminal alkynes with allylic alcohols to access 1,4-enynes.

Chemical Properties

White crystals or crystalline powder

Uses

suzuki reaction

Upstream product

• 13716-10-4 di(tert-butyl)chlorophosphine 
• 213697-67-7 2'-bromo-N,N-dimethyl-[1,1'-biphenyl]-2-amine 
• 694-80-4 2-bromo-1-chlorobenzene 
• 698-01-1 1-chloro-2-(dimethylamino)benzene 
• 698-00-0 2-bromo-N,N-dimethylaniline 

Downstream Products

• 891865-53-5 1-methoxy-N,1-diphenyl-4-indanamine 
• 891865-50-2 bis(3-phenyl-1H-inden-7-yl) ether 
• 1445085-92-6 C₂₂H₃₂NP*C₁₃H₁₃NO₃PdS 

Relevant academic research and scientific papers

The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Phosphine Ligands

Biphenyl-based phosphine ligands can be prepared on a significantly larger scale than previously possible as a result of the following discoveries and improvements to the original experimental procedure: the finding that CuCl catalyzes the coupling of hindered dialkylchlorophosphines with Grignard reagents; the development of conditions that permit ClPCy2 to be prepared and utilized in situ; the development of a more reliable large-scale preparation of 2-dimethylaminophenylmagnesium halide.

An Improved Synthesis of Functionalized Biphenyl-Based Phosphine Ligands

Functionalized dicyclohexyl- and di-tert-butylphosphinobiphenyl ligands are prepared by the reaction of arylmagnesium halides with benzyne, followed by the addition of a chlorodialkylphosphine. This one-pot procedure is considerably less expensive and time-consuming than the method used previously to prepare such ligands. The cost of introducing the dicyclohexylphosphine group can be decreased by preparing chlorodicyclohexylphosphine from PCl3 and cyclohexylmagnesium chloride, and using the reagent without further purification. The new method is significant, as a variety of ligands can be produced in useful amounts by a procedure that is simple, with starting materials that are relatively inexpensive, and, in most cases, without chromatographic purification.

Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers

A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.