13145-84-1

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 1079-66-9 chloro-diphenylphosphine 
• 603-35-0 triphenylphosphine 
• 66107-33-3 3-methoxyphenyl triflate 
• 766-85-8 3-methoxy-1-iodobenzene 
• 829-85-6 diphenylphosphane 
• 95278-09-4 (3-methoxylphenyl)diphenylphosphine oxide 

Downstream Products

• 107629-39-0 (3-Methoxy-phenyl)-methyl-diphenyl-phosphinium-tetraphenylboranat 
• 854937-67-0 3-(diphenylphosphinoyl)-2-iodo-phenol 
• 854937-68-1 (S)-2-Acetoxy-propionic acid 3-(diphenyl-phosphinoyl)-2-iodo-phenyl ester 
• 133545-14-9 (2-iodo-3-methoxyphenyl)diphenylphosphine oxide 
• 32341-36-9 m-hydroxyphenyl(diphenyl)phosphine sulfide 
• 1198151-80-2 (N,N,N',N'-tetraethyl)diamidothiophophosphoric acid O-(3-diphenylthiophosphoryl)phenyl ester 
• 1198151-79-9 (N,N,N',N',-tetramethyl)diamidothiophophosphoric acid O-(3-diphenylthiophosphoryl)phenyl ester 
• 1198151-82-4 methylthiophosphonic acid O-butyl-O-(3-diphenylthiophosphoryl)phenyl ester 
• 1198151-81-3 diphenylthiophosphonic acid O-(3-diphenylthiophosphoryl)phenyl ester 
• 133545-15-0 (Sa)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) 
• 133545-15-0 (Ra)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) 
• 133545-15-0 (RS)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine oxide) 
• 133545-16-1 (-)-(S)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) 
• 133545-16-1 (+)-(R)-(6,6'-dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) 

Relevant academic research and scientific papers

Wittig reactions in water. Synthesis of new water-soluble phosphonium salts and their reactions with substituted benzaldehydes

We report the synthesis of new phosphonium salts which are soluble and stable in basic aqueous solution. The Wittig reactions of these phosphonium salts with substituted benzaldehydes in aqueous sodium hydroxide are discussed. These reactions exclude the use of any organic solvents and the products are isolated by a simple filtration.

Synthesis of aryl phosphines by phosphination with triphenylphosphine catalyzed by palladium on charcoal

The palladium-catalyzed phosphination of aryl bromides and triflates by phosphination with triphenylphines to yield aryl phosphines was catalyzed by the thermally stable catalyst palladium on charcoal.

Synthesis of aryl phosphines via phosphination with triphenylphosphine by supported palladium catalysts

The palladium catalyzed phosphination of functionalized aryl bromides, triflates, and chlorides with triphenylphosphine to yield aryldiphenylphosphines was catalyzed by thermally stable palladium catalysts supported on charcoal and aluminia. The addition

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.

Ionic interaction as a powerful driving force for the formation of heterobidentate assembly ligands

An ionic interaction has been used for the first time to assemble monophosphane ligands. NMR spectroscopy and X-ray studies show that cationic and anionic triphenylphosphane derivatives form ion pairs and subsequently act as a ligand in various transition-metal complexes. The position of the ionic functional groups allows both cis and trans coordination of the novel assembly ligand in square-planar transition-metal complexes.

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.

Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst

The general reduction of phosphine oxides, sulfoxides, and amine N-oxides was achieved by combining bis(2-chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2-chlorophenyl)borinic acid as a precatalyst.

Synthesis, spectroscopy, and electrochemistry of ionic hosts for organic electronics

We report on charge- and ion-transport ionic hosts made from an imidazolium-cation-modified aryl-1,2,4-triazole, phosphineoxide-carbazole, and phosphineoxide. The hosts are white solids that have short-wavelength absorption cut-off at 355 nm (high-energy

Novel phosphite palladium complexes and their application in C-P cross-coupling reactions

A mono- and a 1,3-bis-phosphite arene ligand based on 2,2′-biphenol have been synthesized in order to study the synthesis of the corresponding palladium(II) complexes starting from different Pd precursors. Novel bis-phosphite palladium complex 1 [PdCl2(L)2] (L = dibenzo[d,f][1,3,2]dioxaphosphepin, 6-phenoxy), C,P-chelate bonded monophosphite palladium complex 2 [Pd(κ2-L)(μ-Cl)]2, and PCP-pincer palladium complex 3 have been prepared from these ligands in promising to excellent yields (50-95%). Additionally, complexes 1 and 3 have been characterized by X-ray crystal structure determinations. The application of 2,6-bis-phosphite pincer palladium(II) complex 3 in C-P cross-coupling between diphenylphosphine-borane and a wide range of various aryl iodides under very mild conditions is reported. Kinetic investigations indicate that 3 merely acts as a pre-catalyst and that Pd nanoparticles are the actual catalytically active species.

5,6-Membered palladium pincer complexes of 1-thiophosphoryloxy-3- thiophosphorylbenzenes. Synthesis, X-ray structure, and catalytic activity

Novel unsymmetrical ligands, 1-thiophosphoryloxy-3-thiophosphorylbenzenes 3a-d, bearing phosphine sulfide and thiophosphoryloxy moieties as coordinating sites, were found to undergo cyclometalation at the C-2 position of the central benzene ring in a reac