376355-58-7

Basic information

• Product Name: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][
• Synonyms: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][;BIPOL-A1(S), (S,S)-N-(5,7-Diox-6-phosphadibenzo[a,c]cyclohepten-6-yl)bis(1-phenylethyl)amine, O,Oμ-(2,2μ-Biphenyldiyl) N,N-bis[(S)-1-phenylethyl]phosphoramidite;N,N-Bis[(1S)-(-)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine;N,N-Bis[(1R)-(+)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine;1,1'-Biphenyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite;N,N-bis[(1R)-1-phenylethyl]-Dibenzo[d,f][1,3,2]dioxaphosphepin-6-aMine;Biphenyl-2,2'-diyl bis((1S)-1-phenylethyl)phosphoramidite
• CAS NO: 376355-58-7
• Molecular Formula: C₂₈H₂₆NO₂P
• Molecular Weight: 439.492
• Product Categories: phosphine-amine ligand;Chiral Phosphine;CPN
• Mol File: 376355-58-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 99-102 °C
• Boiling Point: 578.426°C at 760 mmHg
• Flash Point: 303.621°C
• Appearance: white/Powder
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.31±0.20(Predicted)
• Sensitive: moisture sensitive
• CAS DataBase Reference: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(CAS DataBase Reference)
• NIST Chemistry Reference: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(376355-58-7)
• EPA Substance Registry System: N N-BIS-[(S)-1-PHENYLETHYL]DIBENZO[D F][(376355-58-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 376355-58-7(Hazardous Substances Data)

Usage

Reaction

Ligand for the copper catalyzed, highly regioselective substitution reactions of a wide variety of aromatic substituted allylic halides to form branched chiral products from diverse Grignard reagents. Ligand for the copper catalyzed, highly enantioselective conjugate addition of diethylzinc to eneones and nitro olefins. Ligand for the nickel catalyzed, highly enantioselective hydrovinylation of alkenes. Ligand for the rhodium catalyzed, highly enantioselective hydroformylation of vinylarenes. Ligand for gold catalyzed asymmetric Intramolecular hydroamination of allenes

Uses

N,N-Bis-((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine can be used:In the iridium catalyzed allylic arylation.To prepare a copper complex (Cu2X2L3), which is used to detect the transmetalation intermediates in asymmetric addition reactions using ZnEt2.

InChI:InChI=1/C28H26NO2P/c1-21(23-13-5-3-6-14-23)29(22(2)24-15-7-4-8-16-24)32-30-27-19-11-9-17-25(27)26-18-10-12-20-28(26)31-32/h3-22H,1-2H3/t21-,22-/m0/s1

Upstream product

• 1806-29-7 2,2'-dihydroxybiphenyl 
• 21003-56-5 (1S,1'S)-bis(1-phenylethyl)amine 
• 777067-25-1 [(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride 
• 40648-92-8 hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine 
• 16611-68-0 6-chloro-dibenzo[d,f][1,3,2]-dioxaphosphepin 

Relevant articles and documents

On the use of phosphoramidite ligands in copper-catalyzed asymmetric transformations with trialkylaluminum reagents

Phosphoramidites based on BINOL readily react with trimethylaluminum in "noncoordinating" solvents, leading to the corresponding aminophosphine which is the real ligand in copper-catalyzed asymmetric transformations. This artifact explains the experimenta

Efficient, selective, and green: Catalyst tuning for highly enatioselective reactions of ethylene

Fine tuning of the biaryl and amino moieties of Feringa's phosphoramidite ligands yields structurally simpler, yet more efficient and selective, ligands for asymmetric hydrovinylation of vinylarenes and acylic 1,3-dienes. The enantioselectivities and yields observed in the formation of the 3-arylbutenes are among the highest for all asymmetric catalytic processes reported to date for the synthesis of intermediates for the widely used antiinflammatory 2-arylpropionic acids including naproxen, ibuprofen, fenoprofen, and flurbiprofen.

Rh-catalyzed enantioselective conjugate addition of arylboronic acids with a dynamic library of chiral tropos phosphorus ligands

A library of 19 chiral tropos phosphorus ligands, based on a free-to-rotate (tropos) biphenol unit and a chiral P-bonded alcohol (11 phosphites, 1-P(O)2O to 11-P(O)2O) or secondary amine (8 phosphoramidites, 12-P(O)2N to 19-P(O)2N). were screened, individually and in combinations of two, in the rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to enones and enoates. High enantioselectivities (up to 99% ee) and excellent yields were obtained in the addition to either cyclic or acyclic substrates. The flexible biphenolic P ligands outperformed the analogous rigid binaphtholic P ligands. Variable-temperature 31P NMR studies revealed that the biphenolic ligands are tropos even at low temperature. Only below 190 K was a coalescence observed: upon further cooling, two atropisomers were detected. The Rh homocomplexes ([Rh(La)2]+) were also studied: in general, a single doublet (P-Rh coupling) was observed in the case of the biphenolic phosphite ligands, over the temperature range 380-230 K, demonstrating their tropos nature in the rhodium complexes even at low temperatures. On the other hand, the phosphoramidites showed different behaviors depending on the structure of the ligand and on the nature of the rhodium source. The spectrum at 230 K of the mixture of [Rh(acac)(eth)2] (eth = C2H4) with phosphite 6-P(O)2O and phosphoramidite 19-P(O)2N (the most enantioselective ligand combination in the conjugate addition reaction) revealed the presence of four homocomplexes (total approximately 40%: [Rh(6-P(O)2}2], [Rh{(aR)-19-P(O)2N}2], [Rh((aS)-19-P(O)2N) 2], [Rh((aR)-19-P(O)2N}((aS)-19-P(O)2N}]) and one heterocomplex, [Rh{6-P(O)2O){(aR)-19-P(O)2NJ] (approximately 60%) In the heterocomplex, the biphenol-derived phosphite is free to rotate (tropos) while the biphenol-derived phosphoramidite shows a temperature-dependent tropos/atropos behavior (coalescence temperature = 310 K).