16611-68-0Relevant academic research and scientific papers
Synthesis, antioxidant and antimicrobial activity of novel benzene-1,4-diamine-bis-dioxaphosphepine-6λ5 iminophosphoranes
Veera Narayana Reddy,Chandra Sekhar Reddy,Suresh Kumar,Suresh Reddy,Naga Raju
, p. 538 - 542 (2010)
(Chemical Equation Presented). A new class of novel benzene-1,4-diamine- bis-dioxaphosphepine-6λ5 iminophosphoranes (5a-j) were synthesized by the reaction of 6-chlorodibenzo[d,f][1,3,2]dioxaphosphepine (2) with 1,4-diaminobenzene to form bis-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl- benzene-diamine (3). Its subsequent reaction with different alkyl/aryl azides (4a-j) in tetrahydrofuran at 50-60°C under inert atmosphere yielded title compounds. Their structures were established by elemental analysis, IR, 1H, 13C, 31P NMR, and mass spectral studies. All the title compounds were screened for antioxidant properties and found to exhibit potent in vitro antioxidant and antimicrobial activity.
Asymmetric synthesis. Part 29: Asymmetric hydroformylation of styrene catalyzed by chiral spiro diphosphite-rhodium(I) complexes
Jiang, Yaozhong,Xue, Song,Li, Zhi,Deng, Jingen,Mi, Aiqiao,Chan, Albert S. C.
, p. 3185 - 3189 (1998)
Chiral diphosphite ligands L1-L3 were prepared by the reaction of (1S,5S,6R)-(cis,trans)-spiro[4.4]nonane-1,6-diol with chlorophosphites. These ligands were tested in the rhodium catalyzed hydroformylation of styrene and enantioselectivities up to 69% were achieved. High regioselectivities (97%) to 2-phenylpropanal and high yields (98%) were obtained under mild reaction conditions. The influence of reaction conditions is also discussed.
Asymmetric induction by the cholestanic moiety on Tropos species: Synthesis and stereochemical characterization of bile acid-based biphenyl phosphites
Iuliano,Facchetti,Uccello-Barretta
, p. 4943 - 4950 (2006)
Three different bile acid-derived biphenyl phosphites were synthesized, starting from cholic and deoxycholic acids and biphenol, and their stereochemical features were checked by CD and NMR spectroscopies. On the basis of the spectroscopic results, the ca
Enantioselective Synthesis of Planar-Chiral 1, n -Dioxa[ n ]paracyclophane-Based Phosphites and Their Application as Chiral Ligands
Shibata, Takanori,Fukai, Miku,Sekine, Ryosuke,Hazra, Madhurima,Kanyiva, Kyalo Stephen
, p. 2664 - 2670 (2016)
Various planar-chiral 1,n-dioxa[n]paracyclophanes possessing a phenolic hydroxyl group have been synthesized via enantioselective ortho-lithiation. Subsequent reaction with 2,2′-biarylene phosphorochloridites gave a new family of chiral phosphites. These phosphites were then used as chiral ligands in the enantioselective palladium-catalyzed allylic alkylation of dimethyl malonate with (E)-1,3-diphenylallyl acetate and the rhodium-catalyzed 1,4-addition of phenylboronic acid to cyclohex-2-enone.
Rh-Catalyzed Stereospecific Synthesis of Allenes from Propargylic Benzoates and Arylboronic Acids
Ruchti, Jonathan,Carreira, Erick M.
, p. 2174 - 2176 (2016)
An enantiospecific approach to the synthesis of optically active, trisubstituted allenes from chiral propargylic benzoates and arylboronic acids has been developed. The transformation is catalyzed by a Rh-(P,olefin) complex formed in situ from [{Rh(cod)Cl
Complexing and catalytic properties of easily available chiral iminophosphite based on biphenyl-2,2′-diol
Tsarev,Kabro,Moiseev,Kalinin,Bondarev,Davankov,Gavrilov
, p. 814 - 818 (2004)
A chiral iminophosphite ligand based on biphenyl-2,2′-diol and its chelates with rhodium(I) and palladium(II) were synthesized for the first time. Successful use of these compounds in asymmetric allylic substitution was demonstrated. The enantioselectivity of palladium-catalyzed alkylation of methyl pent-3-en-2-yl carbonate with dimethyl malonate reached 70%, that in the alkylation of 1,3-diphenylallyl acetate with dimethyl malonate was 88%. In the rhodium-catalyzed sulfonylation of 1,3-diphenylallyl acetate with sodium p-toluenesulfinite, the enantioselectivity was 56%.
Rh(I) complexes with new C2-symmetric chiral diphosphoramidite ligands: Catalytic activity for asymmetric hydrogenation of olefins
Drommi, Dario,Arena, Carmela Grazia
, (2017)
The design and synthesis of three new C2-symmetric chiral diphosphoramidite ligands starting from simple and cheap building blocks have been developed. Rhodium(I) cationic complexes bearing these chelate ligands have been prepared and applied in asymmetric hydrogenation of model olefins. A rhodium complex with a diphosphoramidite containing a chiral diamine configurationally stable and two fluxional chiral biphenyl units gave higher enantioselectivity with increasing hydrogen pressure (87% ee) in the hydrogenation of dimethyl itaconate.
Rhodium catalysed asymmetric hydroformylation with chiral diphosphite ligands
Buisman,Kamer,Van Leeuwen
, p. 1625 - 1634 (1993)
Chiral diphosphites have been synthesised starting from 1,2:5,6-diisopropylidene-D-mannitol, L-α,α,α,α,-tetramethyla-1,3-dioxolan-4,5-dimethanol and L-diethyltertrate. The diols react in moderate to good yields with 2,2'-bisphenoxyphosphorus chloride and 4,4'6,6',-tetra-t-butyl-2,2'-bisphenoxyphosphorus chloride (32-92%) to the corresponding chiral diphosphites. The compounds all exhibit C2 symmetry and have been used as ligands in the rhodium catalysed asymmetric hydroformylation of styrene. The catalytic activity of the diphosphites strongly depends on the bulkynes of the ligand. With a bulky ligand enantiomeric excesses up till 20% have been obtained under mild reaction conditions (25-40°C, 40 bar syngas). It was found that both enantiomeric excess and regioselectivity to the branched aldehyde strongly depend on the hydroformylation reaction conditions.
Purification method and application of 2, 2 '-biphenoxy phosphorus-chlorine compound
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Paragraph 0078-0081; 0085-0088; 0092-0095; 0098-0101; 0104, (2021/03/13)
The invention provides a purification method and application of a 2, 2 '-biphenoxy phosphorus-chlorine compound, and the purification method comprises the following steps: after the reaction of a 2, 2'-biphenol compound and phosphorus trichloride is finished, adding a composition of organic amine and a mixed solvent to carry out program temperature control distillation purification to obtain the 2, 2 '-biphenoxy phosphorus-chlorine compound; the purification method can effectively reduce the concentration of residual hydrogen chloride, phosphorus trichloride and incompletely reacted aryloxy phosphorus dichloride in reactants, improves the yield and purity of the 2, 2 '-biphenoxy phosphorus-chlorine compound, can effectively improve the yield and purity of bisphosphite when being used in the synthesis of bisphosphite, can effectively reduce content of phosphorus impurities, acid and chloride ions in the bisphosphite is effectively reduced, and meets various requirements of industrial application control indexes.
Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones
Polishchuk, Iuliia,Sklyaruk, Jan,Lebedev, Yury,Rueping, Magnus
supporting information, p. 5919 - 5922 (2021/03/08)
Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.
