54722-12-2

Upstream product

• 108-86-1 bromobenzene 
• 122427-83-2 isopropyl(trimethylsilyl)phosphine 
• 6372-43-6 diisopropylphenylphosphane 
• 75-26-3 isopropyl bromide 
• 638-21-1 phenylphosphane 
• 6372-40-3 isopropyldiphenylphosphine 
• 63762-20-9 (±)-isopropyl(phenyl)phosphine oxide 
• 603-35-0 triphenylphosphine 
• 644-97-3 Dichlorophenylphosphine 
• 172487-18-2 ethyl Phenylphosphinate 

Downstream Products

• 105875-83-0 Isopropyl-octyl-phenyl-phosphane 
• 139936-90-6 4-(Isopropyl-phenyl-phosphanyl)-butyronitrile 
• 565232-59-9 trihydro[isopropyl(phenyl)phosphine]boron 

Relevant academic research and scientific papers

Compound containing phosphine chiral center, organic transition metal complex and preparation method thereof

The invention provides a compound containing a phosphine chiral center, an organic transition metal complex and a preparation method thereof. The preparation method of the compound comprises the following steps: (1) reducing a secondary phosphine oxide 1 into a product secondary phosphine hydrogen 2 by using a reducing agent, wherein the reaction temperature is 20 to 100 DEG C, and the reaction time is 12 to 120 hours; and (2) adding alkyne and the secondary phosphine hydrogen prepared in the step (1) into an organic solvent by using a metal catalyst and a chiral ligand as catalysts to obtain the chiral phosphine compound. The synthesized chiral phosphine compound can be used as a ligand to directly react with transition metal salt to synthesize various organic transition metal complexes. According to the synthesis method disclosed by the invention, secondary phosphine oxide with good stability and low odor is used as a raw material, so that direct use of secondary phosphine with high toxicity and odor for reaction is avoided, and the chiral trivalent phosphine product and the derivative thereof are efficiently and selectively obtained.

Ni-Catalyzed Asymmetric Hydrophosphination of Unactivated Alkynes

The practical synthesis of P-stereogenic tertiary phosphines, which have wide applications in asymmetric catalysis, materials, and pharmaceutical chemistry, represents a significant challenge. A regio- and enantioselective hydrophosphination using cheap a

Chiral Birch reduced tertiary phosphines: Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)

The first examples of an optically active Birch reduced tertiary phosphine, viz. (RP)-(cyclohexa-2,5-dienyl)(3-pentyl)phenylphosphine, and successful hydrophosphination of the related racemic ligand (±)- (cyclohexa-2,5-dienyl)(2-propyl)phenylph

A straightforward synthesis of unsymmetrical secondary phosphine boranes

A one-pot procedure for the synthesis of unsymmetrical alkyl-substituted secondary phosphine oxides is described. The sequential addition of N-benzylaniline to a solution of dichlorophenylphosphine and 1-methylimidazole in methylcyclohexane, separating of the protic ionic liquid formed, addition of Grignard reagent followed by hydrolysis gave unsymmetrical secondary phosphine oxides (SPOs) in high yield. The use of ionic liquids in the first step is essential and streamlined the synthesis. Unsymmetrical SPOs could be quantitatively reduced to secondary phosphine using a catalytic amount of Ti(OiPr)4 and tetramethyldisiloxane (TMDS) under mild reaction conditions.

A superior method for the reduction of secondary phosphine oxides

(Chemical Equation Presented) Diisobutylaluminum hydride (DIBAL-H) and triisobutylaluminum have been found to be outstanding reductants for secondary phosphine oxides (SPOs). All classes of SPOs can be readily reduced, including diaryl, arylalkyl, and dialkyl members. Many SPOs can now be reduced at cryogenic temperatures, and conditions for preservation of reducible functional groups have been found. Even the most electron-rich and sterically hindered phosphine oxides can be reduced in a few hours at 50-70°C. This new reduction has distinct advantages over existing technologies.

A METHOD FOR GENERATING SECONDARY PHOSPHINES

This invention provides a method for generating secondary phosphines from secondary phosphine oxides in the presence of a reducing agent, such as diisobutylaluminum hydride (DIBAL-H), triisobutyldialuminoxane, triisobutylaluminum, tetraisobutyldialuminoxane, or another reducing agent comprising: (i) an R1R2AIH moiety, wherein R1 and R2 are each an alkyl species or oxygen, and wherein at least one of R1 or R2 comprises at least 2 carbon atoms, or (ii) an R1R2R3AI moiety, wherein R1, R2, and R3 are not hydrogen, and wherein at least one of R1, R2, and R3 is an alkyl species comprising a β-hydrogen, not including triethylaluminum. Preferred reducing agents for the present invention include: diisobutylaluminum hydride, triisobutyldialiuminoxane, triisobutylaluminum, tetraisobutyldialuminoxane, and combinations thereof.

Reductive cleavage of the carbon-phosphorus bond with alkali metals. III Reactions of arylalkylphosphines

The reductive cleavage of phenylalkylphosphines Ph2PR, PhPR2 (R = Bu, iPr) with Na/NH3 is unselective; both phenyl and alkyl groups can be cleavaged and Birch reduction may occur.Reaction of Ph2tBuP gives a high yield of diphenylphosphide.Polar groups (CO2Na, SO3Na) at the ω position of primary alkyl groups may lead to an increase in selectivity; Birch reduction is suppressed and a functionalised secondary phosphide is obtained.From diarylbenzyl- and diarylallylphosphines, the benzyl and allyl groups are selectively removed; Ar2PH and ArRPH are formed in high yield after hydrolytic work-up unless the aryl group bears F, CF3 or (CH3)2N substituents.From the reaction mixture of Ph2PCH2Ph we have isolated 1,2-diphenylethane. 2-Methoxyphenyl and 2,6-dimethoxyphenyl groups are selectively removed from Ar2BuP, ArPhBuP and Ar2P(CH2)3PAr2, forming ArBuPH, PhBuPH and ArP(H)(CH2)3(H)PAr, respectively.A double-cleavage reaction of Ar2RP may occur in low yield. 2,6-(dimethoxyphenyl-dibutylphosphine gives dibutylphosphine in moderate yield.When compounds with a 2,6-dimethoxyphenyl moiety are allowed to react with Li/THF, removal of a methyl group leads to novel phosphinophenols.It is concluded that cleavage of alkyl groups R selectively occurs when R radical is relatively stable (tBu, PhCH2> iPr > Bu).

SYNTHESIS OF ASYMMETRIC SECONDARY PHOSPHINES BY THE CROSS COUPLING OF ARYL HALIDES WITH SILYLPHOSPHINES

The cross coupling of aryl halides with alkyl(trimethylsilyl)phosphines catalyzed by zero-valent palladium complexes yields secondary alkylarylphosphoranes containing both electron-donor and electron-withdrawing substituents in the aromatic ring.The rever

A Simple Synthesis and Some Synthetic Applications of Substituted Phosphide and Phosphinite Anions

Based on data for the acidity relationship of phosphines and phosphinous acids and water in dimethyl sulfoxide and water, a simple method is reported for the generation of phosphide and phosphinite anions by the action of concentrated aqueous alkali on primary and secondary phosphines as well as phosphinous acids in dimethyl sulfoxide or other dipolar aprotic solvents.Alkylation of the anion yields secondary and tertiary phosphines, polyphosphines, functionally substituted phosphines as well as similarly substituted phosphine oxides.Phosphinous acids have beenalkylated in various solvents in two-phase systems containing concentrated aqueous alkali and tetrabutylammonium iodide as phase transfer catalyst.