6372-41-4

Usage

InChI:InChI=1/C16H19P/c1-2-3-14-17(15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-13H,2-3,14H2,1H3

Upstream product

• 109-69-3 n-Butyl chloride 
• 591-51-5 phenyllithium 
• 109-72-8 n-butyllithium 
• 1079-66-9 chloro-diphenylphosphine 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 109-65-9 1-bromo-butane 
• 829-85-6 diphenylphosphane 
• 65567-06-8 lithium diphenylphosphide 
• 603-35-0 triphenylphosphine 
• 4233-13-0 butyldiphenylphosphine oxide 
• 17154-34-6 (trimethylsilyl)diphenylphosphine 
• 4376-01-6 sodium diphenylphosphide 
• 18437-78-0 P(p-C₆H₄F)3 
• 1159415-87-8 2-(diphenylphosphanyl)-N-(2'-diphenylphosphanyl-1'-naphthyl)-N'-methyl-1H-benzimidazolium trifluoromethanesulfonate 

Downstream Products

• 4233-13-0 butyldiphenylphosphine oxide 
• 55759-65-4 4-(butyl-phenyl-phosphanyl)-butan-1-ol 
• 59386-53-7 dibutyldiphenylphosphonium bromide 
• 17447-53-9 4,4,5,5-Tetrafluor-2-butyl-diphenyl-phosphoranyliden-cyclopentan-dion-(1,3) 
• 115439-87-7 diphenylbutylbenzylphosphonium chloride 
• 74339-33-6 n-butyldiphenylbenzylphosphonium iodide 
• 76826-08-9 Butyl<3-tert-butyl-5-(diphenylmethyl)-2-hydroxyphenylimino>diphenylphosphoran 
• 10251-55-5 butyl(phenyl)phosphine 
• 334932-59-1 C₂₈H₂₉NO₃P₂ 
• 433-97-6 2-trifluoromethylbenzoic acid 
• 31410-78-3 Ni{P(C₄H₉-n)(C₆H₅)2}4 

Relevant academic research and scientific papers

Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium

We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani

Reductive conversion of phosphoryl P(O) compounds to trivalent organophosphines R3P

By introducing trimethylsilyl chloride (TMSCl), the pentavalent phosphoryl P(V) compounds such as triphenylphosphine oxides, secondary phosphine oxides etc., were readily converted to the corresponding R2P(OTMS) intermediates, that can further react efficiently with an electrophile R'X or with a nucleophile R'Li to produce the corresponding trivalent phosphines R2PR’. Chiral phosphines could also be obtained stereospecifically by this strategy.

Versatile Visible-Light-Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts

Asymmetrically substituted tertiary phosphines and quaternary phosphonium salts are used extensively in applications throughout industry and academia. Despite their significance, classical methods to synthesize such compounds often demand either harsh reaction conditions, prefunctionalization of starting materials, highly sensitive organometallic reagents, or expensive transition-metal catalysts. Mild, practical methods thus remain elusive, despite being of great current interest. Herein, we describe a visible-light-driven method to form these products from secondary and primary phosphines. Using an inexpensive organic photocatalyst and blue-light irradiation, arylphosphines can be both alkylated and arylated using commercially available organohalides. In addition, the same organocatalyst can be used to transform white phosphorus (P4) directly into symmetrical aryl phosphines and phosphonium salts in a single reaction step, which has previously only been possible using precious metal catalysis.

Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium

Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.

Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source

Palladium-catalyzed C(sp3)–P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp3)–P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent.

Direct and Scalable Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine

The direct and scalable electroreduction of triphenylphosphine oxide (TPPO)-the stoichiometric byproduct of some of the most common synthetic organic reactions-to triphenylphosphine (TPP) remains an unmet challenge that would dramatically reduce the cost and waste associated with performing desirable reactions that are mediated by TPP on a large scale. This report details an electrochemical methodology for the single-step reduction of TPPO to TPP using an aluminum anode in combination with a supporting electrolyte that continuously regenerates a Lewis acid from the products of anodic oxidation. The resulting Lewis acid activates TPPO for reduction at mild potentials and promotes P-O over P-C bond cleavage to selectively form TPP over other byproducts. Finally, this robust methodology is applied to (i) the reduction of synthetically useful classes of phosphine oxides, (ii) the one-pot recycling of TPPO generated from a Wittig reaction, and (iii) the gram-scale reduction of TPPO at high concentration (1 M) with continuous product extraction and in flow at high current density.

Mitsunobu Reaction Using Basic Amines as Pronucleophiles

A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.

Alkyl diphenyl phosphine and preparing alkyl diphenyl phosphine payment proportional to production alkyl benzene

The invention discloses alkyl diphenylphosphine and a method for preparing alkyl diphenylphosphine with co-production of alkylbenzene. The structural formula of alkyl diphenylphosphine is shown in a formula I. The method comprises: adding triphenylphosphine and metal lithium into an organic solvent for reaction for 3-6 hours at room temperature; and cooling the reaction system to 0-10 DEG C, adding halogenated straight-chain alkane for insulating reaction, then raising the temperature of the system to 30-80 DEG C, keeping the temperature to react for 1-3 hours, removing the organic solvent and reducing the pressure and distilling to separately obtain alkyl diphenylphosphine and alkylbenzene. According to the alkyl diphenylphosphine disclosed by the invention, alkyl is directly bonded with P, so that the alkyl diphenylphosphine can be dissolved in most solvents and can be used as a ligand for homogeneous catalysts. By virtue of the method disclosed by the invention, high value straight-chain alkylbenzene is co-produced while straight-chain alkyl diphenylphosphine is prepared by way of a one-pot process. Use of chloro-tert-butane which is relatively high in price and waste of the metal lithium are avoided. The method is simple to operate, efficient, low in energy consumption, low in cost and suitable for large-scaled industrial production.

Aryl group - A leaving group in arylphosphine oxides

The treatment of triphenylphosphine oxide with organometallic reagents leads to the substitution of up to three phenyl substituents with the incoming carbon nucleophile. The replacement of the phenyl/aryl group in tertiary diarylalkylphosphine oxides or even aryldialkylphosphine oxides was also observed. Naphthyl-substituted phosphine oxides undergo Michael-type addition at the naphthyl group when treated with organolithium reagent.