29882-18-6

Upstream product

• 1706-96-3 phenyl diphenylphosphinate 
• 104-94-9 4-methoxy-aniline 
• 21713-53-1 4-methyl-o-phenyl phenyl(phenyl)phosphinate 
• 1499-21-4 Diphenylphosphinic chloride 
• 5994-87-6 diphenylphosphinamide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 4559-70-0 Diphenylphosphine oxide 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 2101-87-3 p-methoxy-phenylazide 

Downstream Products

• 1004853-94-4 C₁₇H₁₅NOP⁽¹⁺⁾ 

Relevant academic research and scientific papers

Synthesis of Nonalternating Polyketones Using Cationic Diphosphazane Monoxide-Palladium Complexes

Copolymerization of olefin with carbon monoxide has received considerable interest from both academia and industry, and the introduction of polar carbonyl group renders the resultant polyketones with excellent mechanical strength, crystallinity, photodegr

Redox-Neutral P(O)-N Coupling between P(O)-H Compounds and Azides via Dual Copper and Photoredox Catalysis

We report a redox-neutral P(O)-N coupling reaction of P(O)-H compounds with azides via photoredox and copper catalysis, providing new access to useful phosphinamides, phosphonamides, and phosphoramides. This transformation tolerates a wide range of nucleophilic functionalities including alcohol and amine nucleophiles, which makes up for the deficiency of classical nitrogen nucleophilic substitution reactions. As a demonstration of the broad potential applications of this new methodology, late-stage functionalization of a diverse array of azido-bearing natural products and drug molecules, a preliminary asymmetric reaction, and a continuous visible-light photoflow process have been developed.

Ligand-free copper-catalyzed denitrogenative arylation of phosphorylamides with arylhydrazines

A straightforward arylation of phosphorylamides with arylhydrazines hydrochloride was herein demonstrated. The protocol proceeded in the presence of a catalytic loading of Cu(OAc)2 as the catalyst, DTBP as the external oxidant and Cs2CO3 as the base, but without any ligands. And a series of N-aryl phosphorylamides were successfully obtained in high efficiency (up to 93% yields) with good substituents compatibility (up to 30 examples). Free radical mechanism was proposed for the facile methodology based on the results of control reactions and literature explorations.

Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)?H Compounds

Herein, we report a highly efficient ZnI2-triggered oxidative cross-coupling reaction of P(O)?H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up syntheses as well as late-stage functionalization of drug molecules. The stereospecific coupling is also achieved from readily available optically enriched P(O)?H compounds.

A Versatile Ligand Platform for Palladium- and Nickel-Catalyzed Ethylene Copolymerization with Polar Monomers

The ability to carry out transition-metal-catalyzed copolymerizations of olefins with polar monomers is a great challenge in the field of olefin polymerization. Palladium has been the dominant player in this field, while its low-cost nickel counterpart has only achieved very limited success. We report the synthesis and evaluation of a highly versatile platform based on diphosphazane monoxide ligands. Both palladium and nickel catalysts bearing these ligands mediate the copolymerization of ethylene with a number of fundamental polar monomers.

The Chan-Evans-Lam N-arylation of phosphonic/phosphinic amides

A stoichiometric copper(II)-mediated arylation protocol of phosphinamides and phosphonamides was herein demonstrated. Various unreported N-aryl phosphinamides and phosphonamides were successfully prepared through Chan-Evans-Lam reaction with high efficiency (up to 88% yields) and good functional groups tolerance (30 examples) in the absence of any ligands or co-catalysts.

Insertion of arynes into arylphosphoryl amide bonds: One-step simultaneous construction of C-N and C-P bonds

The insertion of arynes into arylphosphoryl amide bonds to synchronously construct C-P and C-N bonds is described. Arynes generated in situ from o-triflate arylsilanes under fluoride-promoted conditions insert into relatively inert P-N bonds, producing o-

Kinetics and mechanism of the pyridinolysis of N-aryl-P,P-diphenyl phosphinic amides in dimethyl sulfoxide

Kinetic studies for the reactions of Z-N-aryl-P,P-diphenyl phosphinic amides with X-pyridines have been carried out in dimethyl sulfoxide at 85.0 °C. The two strong π-acceptor substituents, X = 4-Ac and 4-CN in the X-pyridine, exhibit positive deviations

Kinetics and mechanism of the anilinolyses of aryl dimethyl, methyl phenyl and diphenyl phosphinates

The reactions of Z-aryl dimethyl (1), methyl phenyl (2), and diphenyl (3) phosphinates with X-anilines in dimethyl sulfoxide at 60.0 °C are studied kinetically. Kinetic results yield the primary normal deuterium kinetic isotope effects (DKIEs) involving deuterated aniline (XC6H4ND 2) nucleophiles, kH/kD = 1.03-1.17, 1.15-1.29, and 1.24-1.51, and the cross-interaction constants (CICs), ρXZ = 0.37, 0.34, and 0.65 for 1, 2, and 3, respectively. The steric effects of the ligands (R1 and R2) on reaction rates play a role, but are relatively much smaller compared to other phosphinate systems. A stepwise mechanism with a rate-limiting leaving group expulsion from the intermediate is proposed on the basis of the CICs positive signs. The dominant frontside nucleophilic attack through a hydrogen-bonded, four-center-type transition state is proposed on the basis of primary normal DKIEs and large magnitudes of the CICs for 2 and 3, while both frontside and backside attack are proposed on the basis of relatively small primary normal DKIEs for 1.

Labile P-C bonds: P-(phosphinoyl)methyl-λ5-phosphazenes and related compounds

N-Aryl-P,P-diphenyl-P-(diphenylphosphinoyl)methyl-λ5-pho sphazenes undergo smooth acid-catalysed hydrolysis with concomitant P-C bond fission yielding N-aryl-P,P-diphenylphosphinamides and diphenylmethylphosphane oxide. A tentative mechanistic explanation is given.