1224869-06-0

Basic information

• Product Name: (S)-3-(diphenylphosphinyl)-1,3-diphenylpropan-1-one
• Synonyms: (S)-3-(diphenylphosphinyl)-1,3-diphenylpropan-1-one
• CAS NO: 1224869-06-0
• Molecular Weight: 410.452
• Mol File: 1224869-06-0.mol

Chemical Properties

• CAS DataBase Reference: (S)-3-(diphenylphosphinyl)-1,3-diphenylpropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(diphenylphosphinyl)-1,3-diphenylpropan-1-one(1224869-06-0)
• EPA Substance Registry System: (S)-3-(diphenylphosphinyl)-1,3-diphenylpropan-1-one(1224869-06-0)

Safety Data

• Hazardous Substances Data: 1224869-06-0(Hazardous Substances Data)

Upstream product

• 1244964-81-5 (S)-Ph₂PCH(Ph)CH₂COPh 
• 4559-70-0 Diphenylphosphine oxide 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 14371-10-9 (E)-3-phenylpropenal 
• 94-41-7 benzalacetophenone 
• 829-85-6 diphenylphosphane 
• 16247-23-7 Diphenyl-(3-oxo-1,3-diphenylpropyl)-phosphin 

Relevant articles and documents

Synthesis of heterodimetallic iridium-palladium complexes containing two axes of chirality: Study of sequential catalytic properties

The reaction of [Cp*Cl2Ir(triazolium-ylidene)]BF 4 (Cp* = pentamethylcyclopentadienyl) with chiral orthometalated palladium dimers results in facile bridge splitting to afford heterodimetallic Ir-Pd* complexes. The structural characteristics of these complexes show the presence of different isomers as a consequence of hindered rotation about the M-Ccarbene bond (M = Ir/Pd). The heterodimetallic complexes contain two axes of chirality related to each metal. The crystal structure of one heterodimetallic iridium-palladium complex derived from the chiral N,N-dimethylbenzylamine ligand is described and contains two of the rotamers. The Ir/Pd* complexes have been tested in a sequence of two catalytic reactions, which implies the isomerization and asymmetric hydrophosphination of 1,3-diphenylpropargyl alcohol. All the catalysts show high activity in the overall reaction process and excellent regioselectivity, although the enantioselectivities were low. The synthesis of iridium/palladium complexes based on the triazolium-diylidene ligand with a chiral chelate C-N ligand is described. The heterodimetallic Ir-Pd* complexes contain two axes of chirality related to each metal. The Ir/Pd* complexes are active in a sequence of two catalytic reactions, thus implying the isomerization and asymmetric hydrophosphination of 1,3-diphenylpropargyl alcohol. Copyright

Asymmetric Synthesis of P-Stereogenic Secondary Phosphine-Boranes by an Unsymmetric Bisphosphine Pincer-Nickel Complex

The first highly enantioselective catalytic synthesis of P-stereogenic secondary phosphine-boranes was realized by the asymmetric addition of primary phosphine to electron-deficient alkenes with a newly developed unsymmetric bisphosphine (PCP′) pincer-nickel complex. Various P-stereogenic secondary phosphine-boranes were obtained in 57-92% yields with up to 99% ee and >20:1 dr. The follow-up alkylation upon P-C bond formation with alkyl halides provided a practical way to access P-chiral compounds with diverse functional groups.

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh2 species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPAr1Ar2) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords P-chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. 1H NMR studies show that the precoordination of HPPh2 to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(R,RP)-TANIAPHOS complex in the presence of excessive HPPh2, confirmed by 31P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh2 would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.

Versatile syntheses of optically pure pce pincer ligands: Facile modifications of the pendant arms and ligand backbones

A series of chiral C-stereogenic PCP and PCN ligand precursors were prepared in situ from inexpensive achiral starting materials via a simple catalytic asymmetric P-H addition reaction in good overall yields. This facile catalytic method of preparing the ligand backbones renders easy and economical modifications of the electronically crucial para-substituent, chiral functionalities, and donor atoms for different transition metal ions. A one-pot synthetic procedure was used efficiently to prepare the corresponding optically pure pincer complexes. All the new complexes were characterized by NMR and mass spectroscopy. The molecular structures of several selected complexes have also been elucidated by X-ray crystallography. Preliminary studies indicated that minor structural changes on these novel pincer complexes affect their chemical properties significantly when they were applied as catalysts for the reaction between diphenylphosphine and chalcone.

PCN pincer palladium(II) complex catalyzed enantioselective hydrophosphination of enones: Synthesis of pyridine-functionalized chiral phosphine oxides as NCsp3O pincer preligands

A series of chiral PCN pincer Pd(II) complexes VI- XIII with aryl-based aminophosphine-imidazoline or phosphinite-imidazoline ligands were synthesized and characterized. They were examined as enantioselective catalysts for the hydrophosphination of enones

Enantioselective hydrophosphination of enones with diphenylphosphine catalyzed by bis(imidazoline) NCN pincer palladium(II) complexes

A series of chiral NCN pincer Pd(II) complexes with 1,3-bis(2′- imidazolinyl)phenyl (Phebim) ligands were synthesized via the C-H activation or oxidative addition method. A dinuclear macrocyclic Pd(II) complex was also prepared by reaction of the Phebim-H

NHC-copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones

N-Heterocyclic carbene-copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones was developed for the synthesis of chiral phosphorus derivatives in high yields with moderate enantioselectivity under mild conditions.

Chiral palladacycles with N-heterocyclic carbene ligands as catalysts for asymmetric hydrophosphination

Design of chiral palladacycles with N-heterocyclic carbene (NHC) ligands has been carried out in good yields starting form commercially available enantiopure benzylamines. The methodology developed consists of the formation of palladium dimers with orthom

Palladium-catalyzed 1,4-addition of diarylphosphines to α,β-unsaturated aldehydes

A highly stereoselective asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated aldehydes catalyzed by a bis(phosphine) pincer-Pd complex has been developed for the synthesis of chiral phosphines with excellent stereoselectivity (up to 98% ee) und

Unsymmetrical chiral PCN pincer palladium(II) and nickel(II) complexes with aryl-based aminophosphine-imidazoline ligands: Synthesis via aryl C-H activation and asymmetric addition of diarylphosphines to enones

Figure Persented: Chiral 3-(2′-imidazolinyl)anilines 3a-c were easily synthesized by converting the carboxyl and nitro groups in commercially available 3-nitrobenzoic acid to chiral imidazoline and amine, respectively. The one-pot phosphorylation/metalati