2572-40-9

Upstream product

• 791-28-6 Triphenylphosphine oxide 
• 88-67-5 2-Iodobenzoic acid 
• 603-35-0 triphenylphosphine 
• 71-43-2 benzene 
• 932-31-0 ortho-tolylmagnesium bromide 
• 6840-26-2 diphenyl-o-tolyl-phosphine oxide 
• 17261-28-8 ortho-diphenylphosphinobenzoic acid 
• 5931-53-3 Diphenyl-o-tolylphosphin 
• 1079-66-9 chloro-diphenylphosphine 

Downstream Products

• 79317-63-8 o-diphenylphosphonylbenzoic acid methyl ester 
• 79184-77-3 P-chloro-P,P-diphenyl-2,3-benzoxaphospholen-1-one 
• 17261-28-8 ortho-diphenylphosphinobenzoic acid 
• 65523-20-8 10-hydroxy-5,10-dimethyl-5-phenyl-5,10-dihydro-acridophosphinium; iodide 
• 65523-18-4 10-hydroxy-5-methyl-5,10-diphenyl-5,10-dihydro-acridophosphinium; iodide 
• 65523-13-9 5-benzyl-10-oxo-5-phenyl-5,10-dihydro-acridophosphinium; chloride 
• 65523-23-1 5-methyl-5,10-diphenyl-5,10-dihydro-acridophosphinium; iodide 
• 61279-12-7 10-methyl-5-phenyl-5,10-dihydro-acridophosphin-10-ol 
• 54086-39-4 5,10-dihydro-10-phenyldibenzophosphorine-5-one 
• 65523-16-2 10-(3-dimethylamino-propyl)-5-phenyl-5,10-dihydro-acridophosphin-10-ol 
• 65523-15-1 5,10-diphenyl-5,10-dihydro-acridophosphin-10-ol 
• 54086-38-3 10-Phenyl-9,10-dihydro-10-λ⁵-acridophosphin-9,10-dion 

Relevant academic research and scientific papers

One-pot palladium-catalyzed phosphination of aryl iodides with Ph2PSnR3

We found a very efficient one-pot phosphination reaction starting with Ph3P, which by reaction with Na metal in liquid ammonia gives Ph2P- ions that reacted with R3SnCl to afford (trialkylstannyl)diphenylphosphine. The palladium-catalyzed coupling reaction of these stannanes with aryl iodides yield functionalized phosphines in high yield (69-97%). The use of Ph3P as starting reagent, the endurance of the reaction to a wide variety of functional groups and the easiness of a one-pot reaction make this method a useful and versatile approach to tertiary phosphine oxides.

Synthesis of tertiary phosphine oxides by alkaline hydrolysis of quaternary phosphonium zwitterions using excess t-BuOK and stoichiometric water

Hydrolysis of quaternary arylphosphonium zwitterions bearing COO? and those in situ generated from the corresponding salts bearing Ac or OH at the aryl ring by using excess t-BuOK and stoichiometric water affords tertiary arylphosphine oxides in moderate to excellent yield, in contrast to hydrolysis of these zwittertion or salts in aqueous NaOH that mainly provides phosphine oxides with the loss of the aryl group. Under the t-BuOK/water conditions, hydrolysis of carbonyl stabilized ylides Ph3P = CHCOR (R = Ph, Me, and OEt), which partially exist as phosphonium enolates, prefers to produce Ph2P(O)CH2COR. Further reduction of Ph2P(O)CH2COMe by PhSiH3 allows the preparation of Ph2PCH2COMe in 43% yield.

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

Tuning the Diiron Core Geometry in Carboxylate-Bridged Macrocyclic Model Complexes Affects Their Redox Properties and Supports Oxidation Chemistry

We introduce a novel platform to mimic the coordination environment of carboxylate-bridged diiron proteins by tethering a small, dangling internal carboxylate, (CH2)nCOOH, to phenol-imine macrocyclic ligands (H3PIMICn). In the presence of an external bulky carboxylic acid (RCO2H), the ligands react with [Fe2(Mes)4] (Mes = 2,4,6-trimethylphenyl) to afford dinuclear [Fe2(PIMICn)(RCO2)(MeCN)] (n = 4-6) complexes. X-ray diffraction studies revealed structural similarities between these complexes and the reduced diiron active sites of proteins such as Class I ribonucleotide reductase (RNR) R2 and soluble methane monooxygenase hydroxylase. The number of CH2 units of the internal carboxylate arm controls the diiron core geometry, affecting in turn the anodic peak potential of the complexes. As functional synthetic models, these complexes facilitate the oxidation of C-H bonds in the presence of peroxides and oxo transfer from O2 to an internal phosphine moiety.

Comparison of Reductive Ligation-Based Detection Strategies for Nitroxyl (HNO) and S-Nitrosothiols

Phosphine-based detection strategies for both nitroxyl (HNO) and S-nitrosothiols (RSNO) were investigated and compared. Phosphorus NMR studies show that azaylides derived from HNO or organic RSNO efficiently participate in subsequent reductive ligation required for fluorescence generation in properly substituted substrates. S-Azaylides derived from biological RSNO containing free amine and carboxylic acid groups primarily yield phosphine oxides suggesting these groups facilitate nonligation pathways such as hydrolysis. The fluorescence response of a phosphine-based fluorophore toward the same RSNO confirms these differences and indicates that these probes selectively react with HNO. Flow cytometry experiments in HeLa cells reinforce the reactivity difference and offer a potential fast screening approach for endogenous HNO sources.

ORTHO-LITHIATION OF TRIPHENYLPHOSPHINO-METHYLID AND, ALSO, TRIPHENYLPHOSPHINE OXIDE

While upon treatment with methyl- or butyllithium triphenylphosphonio-methylid (1) undergoes extensive ligand exchange (leading to 4) it reacts with sec- or tert-butyllithium mainly at the ortho-position exchanging one hydrogen against a lithium atom (to give 3).