Sep-21 News Final Thoughts on Chemistry for [1,1′-Binaphthalene]-2,2′-diamine

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A facile route to the synthesis of 1,1?-binaphthyl-4,4?- diamines (naphthidines) and 1,1?-binaphthyl-2,2?-diamines (BINAMs) was developed by the oxidative homocoupling of 1- and 2-naphthylamines, respectively, using FeCl3 as oxidant and K2CO3 as base in 1,2-dichloroethane under ambient conditions. A preliminary mechanistic investigation was performed by the ESR spectroscopy and intermediate-trapping technique.

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Reference:
Chiral Catalysts,
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23-Sep-21 News Archives for Chemistry Experiments of [1,1′-Binaphthalene]-2,2′-diamine

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Chiral salen-metal complexes have been tested as catalysts for the C-alkylation of Schiff’s bases of alanine and glycine esters with alkyl bromides under phase-transfer conditions (solid sodium hydroxide, toluene, ambient temperature, 1-10 mol% of the catalyst). The best catalyst, which was derived from a Cu(II) complex of (1R, 2R or 1S,2S)-[N,N?-bis(2?-hydroxybenzylidene)]-1,2-diaminocyclohexane, gave alpha-amino and alpha-methyl-alpha-amino acids with enantiomeric excesses of 70-96%.

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Chiral Catalysts,
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9/22/21 News Extended knowledge of [1,1′-Binaphthalene]-2,2′-diamine

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.4488-22-6, Name is [1,1′-Binaphthalene]-2,2′-diamine, molecular formula is C20H16N2. In a Article,once mentioned of 4488-22-6, Recommanded Product: [1,1′-Binaphthalene]-2,2′-diamine

A cobalt(iii) complex (1) of a salcy-type ligand tethering 4 quaternary ammonium salts, which is thought to act as a highly active catalyst for CO 2/propylene oxide (PO) copolymerization, also shows high activity (TOF, 25900 h-1; TON, 518000; 2.72 kg polymer per g cat) and selectivity (>98%) for CO2/ethylene oxide (EO) copolymerization that results in high-molecular-weight polymers (Mn, 200000-300000) that have strictly alternating repeating units. The related cobalt(iii) complexes 11-14 were prepared through variations of the ligand framework of 1 by replacing the trans-1,2-diaminocyclohexane unit with 2,2-dimethyl-1,3- propanediamine, trans-1,2-diaminocyclopentane, or 1,1?-binaphthyl-2, 2?-diamine or by replacing the aldimine bond with ketimine. These ligand frameworks are thought to favour the formation of the cis-beta configuration in complexation, and the formation of the cis-beta configuration in 11-14 was confirmed through NMR studies or X-ray crystallographic studies of model complexes not bearing the quaternary ammonium salts. Complexes 11, 13, and 14, which adopt the cis-beta configuration even in DMSO did not show any activity for CO2/PO copolymerization. Complex 12, which was constructed with trans-1,2-diaminocyclopentane and fluctuated in DMSO between the coordination and de-coordination of the acetate ligand as observed for 1, showed fairly high activity (TOF, 12400 h-1). This fluctuating behaviour may play a role in polymerization. However, complex 12 did not compete with 1 in terms of activity, selectivity, and the catalyst cost.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare

17-Sep-21 News A new application about [1,1′-Binaphthalene]-2,2′-diamine

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3,5-Dinitrobenzoyl chloride was previously used for the preparation of (R)-phenylglycinol- and (S)-leucinol-derived chiral stationary phases. In this study, 3,5-bis(trifluoromethyl)benzoyl chloride, 2-furoyl chloride, 2-theonyl chloride, 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonyl chloride, diphenylcarbamoyl chloride, and 1-adamantanecarbonyl chloride were used to prepare six new phenylglycinol-derived chiral stationary phases (CSPs) and five new leucinol-derived CSPs. Using these 11 CSPs, chiral separation of nine pi-acidic amino acid derivatives and five pi-basic compounds was performed, and the separation results were compared. An adamantyl-derived CSP showed good separation.

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Reference:
Chiral Catalysts,
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Sep-21 News Discovery of [1,1′-Binaphthalene]-2,2′-diamine

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Palladium-catalysed aminocarbonylation of a terpenoic iodoalkene (2-iodo-bornene) model compound with both enantiomerically pure and racemic 2,2?-diamino-1,1?-binaphthalene (BINAM) as the N-nucleophile was carried out. All of the diastereoisomers of the monocarboxamide (N-bornenyl carboxamide) and dicarboxamide (N,N?-dinorbornenylcarboxamide) derivatives were synthesised. The diastereoselectivities of the aminocarbonylation were investigated in both cases: either racemic BINAM was used as the N-nucleophile in the aminocarbonylation of enantiomerically pure 2-iodobornene or racemic iodobornene was aminocarbonylated with enantiomerically pure BINAM with moderate diastereoselectivities. In this way, all possible diastereoisomers of binaphthalene-bornene conjugates were synthesised in moderate to high yields by asymmetric (diastereoselective) aminocarbonylation.

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14-Sep-2021 News Final Thoughts on Chemistry for [1,1′-Binaphthalene]-2,2′-diamine

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The dilithium diamides [{Li(thf)}2{C20H12(NR)2}] (R = SiMe3 1 or CH2But 2, thf = tetrahydrofuran) were prepared from R,S-2,2?-diamino-1,1?-binaphthyl, C20H12(NH2)2, via C20H12[N(H)SiMe3]2 or C20H12[NHC(O)But]2 and C20H12[N(H)CH2But]2, respectively, and were transformed into SiCl2[C20H12(NR)2] by treatment with SiCl4. The crystal structures of 1 and 2 were determined. They are monomers, having a Li(1)N(1)Li(2)N(2) buckled ring, with Li(1)-N(2) ca. 0.2 A shorter than Li(1)-N(1), the two groups R cis to one another, and N(1)-C(1) eta2 bonded to Li(1). The R and S enantiomers were similarly prepared and their optical stability was demonstrated by their hydrolysis to R- and S-C20H12(NH2)2, respectively. Evidence is provided for the structures of [M{C20H12[N(SiMe3)]2}] (M = Ge or Sn), obtained by conversion of the stannylene into the crystallographically characterised [{Sn[(NSiMe3)2C20H12](mu-O)} 3].

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare

Sep 2021 News Top Picks: new discover of [1,1′-Binaphthalene]-2,2′-diamine

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The synthesis of new chiral salenophos-type ligands bearing ‘hard’ and ‘soft’ coordination sites is described. The polyfunctionalised ligands are used for the construction of monometallic and early-late heterobimetallic complexes. In the reaction with titanium(IV) reagents the salen subunit selectively coordinated to the ‘hard’ metal. The phosphine groups in turn can be coordinated to rhodium(I). The coordination geometry of the diphosphine- Rh subunit is strongly influenced by the counter ligands COD or CO and Cl, respectively. In the asymmetric hydroformylation of vinyl acetate with one of the Rh-Ti-complexes, the branched aldehyde is predominantly formed with 30% ee.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare

6-Sep-2021 News Extended knowledge of [1,1′-Binaphthalene]-2,2′-diamine

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Mono-N-alkylated octahydrobinaphthyl-2,2?-diamine (H 8-BINAM) chiral ligands were employed in the catalytic and asymmetric oxidative coupling of methyl 3-hydroxy-2-naphthoate to the corresponding binaphthol derivative. The diamine ligand with one N-(3-pentyl) group shows highest enantioselectivity in the biaryl coupling among other BINAM derivatives, and the coupling reaction proceeds faster than the reactions using alkanediamine ligands.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare

03/9/2021 News Top Picks: new discover of [1,1′-Binaphthalene]-2,2′-diamine

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A wide range of diaryl thioethers and aryl alkyl thioethers are synthesized from the corresponding aryl iodides and aromatic/aliphatic thiols through Ullmann type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-Cu(OTf)2 complex. Less reactive aryl bromides have also been shown to react with thiols under identical reaction conditions to give good yields of the thioethers without increasing the reaction temperature and time.

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Reference:
Chiral Catalysts,
Chiral catalysts – SlideShare

03/9/2021 News Discovery of [1,1′-Binaphthalene]-2,2′-diamine

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A dimeric proline derived diamidobinaphthyl dilithium salt represents the first example of a chiral main group metal based catalyst for asymmetric hydroamination/cyclisation reactions of aminoalkenes. The Royal Society of Chemistry 2006.

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Reference:
Chiral Catalysts,
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