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Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 112-54-9 Dodecanal 
• 629-23-2 tetradecan-3-one 
• 5981-19-1 5-undecyl-1,2-oxathiolane 2,2-dioxide 
• 629-59-4 tetradecane 
• 557-20-0 diethylzinc 
• 917-54-4 methyllithium 
• 1713-31-1 (R)-(+)-1,2-epoxytridecane 
• 30608-62-9 (S)-(-)-1,2-epoxybutane 
• 112-29-8 1-bromo dodecane 
• 143-07-7 lauric acid 
• 123-38-6 propionaldehyde 

Relevant academic research and scientific papers

A new organo-ruthenium substituted tungstotellurate: Synthesis, structural characterization and catalytic properties

Reaction of [RuC6H6Cl2]2 with TeO2 and Na2WO4·2H2O in aqueous solution (pH 4.7) yielded a novel organo-ruthenium supported tungstotellurate polyanion, [Te2W20O70(RuC6H6)2]8- (Ru-1), which is composed of two [RuC6H6]2+ units linked to a [Te2W20O70]12- fragment through Ru-O(W) bonds resulting in an assembly with idealized C2h symmetry. Furthermore, the polyanion Ru-1 was anchored on 3-aminopropyltriethoxysilane (apts)-modified SBA-15 to prepare new catalysts (SBA-15-apts-Ru-1) containing different amounts of Ru-1, which were characterized using powder X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), N2-adsorption measurement and Fourier transform infrared reflectance (FT-IR) spectroscopy. Finally, the catalytic activity of SBA-15-apts-Ru-1 was evaluated for the aerobic oxidation of n-tetradecane using air as the oxidant in the absence of any additives or solvents. In addition, the optimum catalytic reaction conditions were also determined.

3,3′-diphosphoryl-1,1′-bi-2-naphthol-Zn(II) complexes as conjugate acid-base catalysts for enantioselective dialkylzinc addition to aldehydes

A highly enantioselective dialkylzine (R22Zn) addition to a series of aromatic, aliphatic, and heteroaromatic aldehydes (5) was developed based on conjugate Lewis acid-Lewis base catalysis. Bifunctional BINOL ligands bearing phosphine oxides [P(=O)R2] (7), phosphonates [P(=O)(OR)2] (8 and 9), or phosphoramides [P(=O)(NR2) 2] (10) at the 3,3′-positions were prepared by using a phospho-Fries rearrangement as a key step. The coordination of a NaphO-Zn(II)-R2 center as a Lewis acid to a carbonyl group in a substrate and the activation of R22Zn(II) with a phosphoryl group (P=O) as a Lewis base in the 3,3′-diphosphoryl-BINOL- Zn(II) catalyst could promote carbon-carbon bond formation with high enantioselectivities (up to >99% ee). Mechanistic studies were performed by X-ray analyses of a free ligand (7) and a tetranuclear Zn(II) cluster (21), a 31P NMR experiment on Zn(II) complexes, an absence of nonlinear effect between the ligand (7) and Et-adduct of benzaldehyde, and stoichiometric reactions with some chiral or achiral Zn(II) complexes to propose a transition-state assembly including monomeric active intermediates.

Enantioselective addition of organozinc reagents to aldehydes catalyzed by 3,3′-bis(diphenylphosphinoyl)-BINOL

The enantioselective addition of organozinc reagents to aromatic and aliphatic aldehydes 1 gives secondary alcohols 2 with excellent enantioselectivities in high yields through the catalytic use of (R)-3,3′-bis(diphenylphosphinoyl)-BINOL (3) or (R)-3,3′- bis(diphenylthiophosphinoyl)-BINOL (4) without Ti(IV) complexes. The coordination of the O or S atom of a (thio)phosphinoyl group bearing a BINOL backbone to organozinc reagents can efficiently increase the nucleophilicity of the organozinc reagents.

Synthesis of C2-symmetrical bis-β-amino alcohols and their application in the enantioselective addition of diethylzinc to aldehydes

The C2-symmetrical bis-β-amino alcohols 1-6 were prepared and especially attention is focused on bridges, which link the two β-amino alcohol units. These ligands have been applied as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes. sec-Alcohols have been obtained in good yields with up to 95.4% enantiomeric excess.

Shape Selective Alkane Hydroxylation by Metalloporphyrin Catalysts

A series of manganese and iron porphyrins with sterically protected pockets are shown to be shape selective alkane hydroxylation catalysts.With iodosobenzene as oxidant, good regioselectivity is observed for hydroxylation of alkanes at the least hindered methyl group by using the very sterically hindered (5,10,15,20-tetrakis(2',4',6'-triphenylphenyl)porphyrinato)manganese(III) acetate (MnTTPPP(OAc)) as catalyst; The moderately hindered (5,10,15,20-tetrakis(2',4',6'-trimethoxyphenyl)porphyrinato)manganese(III) acetate shows little selectivity toward terminal CH3 hydroxylation but does show enhancement for the adjacent, ω - 1, CH2 site.Primary selectivity is dependent on the size and shape of the alkane substrate, with more bulky substituents giving greater primary selectivity.Substituting pentafluoroiodosobenzene or m-chloroperbenzoic acid as oxidants yields similar selectivity, thus conclusively demonstrating metal based oxidation via a common intermediate for these three systems.In contrast, tert-butyl hydroperoxide or 2,2,2-trifluoroethanol solubilized pentafluoroiodosobenzene show no primary carbon selectivity, and reaction product ratios are independent of the metalloporphyrin catalyst; this demonstrates that the site of oxidation with these oxidants is not metal based.The iron porphyrin derivatives also show good primary selectivity, although to a lesser degree than with the Mn derivatives, proving that these oxidations too are metal based.The regioselectivities for alkane hydroxilation shown by TTPPP derivatives are comparable to or better than those found for some isozymes of cytochrome P-450 which are responsible for primary alcohol biosynthesis from steroids, fatty acids, and alkanes.

Shape-selective Alkane Hydroxylation

A series of sterically hindered manganese porphyrins have been used to catalyse shape-selective alkane hydroxylation, increasing the production of primary alcohols.

Lithium aluminum hydride-aluminum hydride reduction of sultones

Lithium aluminum hydride-aluminum hydride reduction of secondary and tertiary (C-O) substituted γ-sultones or α-alkyl-β'-hydroxy γ-sultones yields mercapto alcohols and mercapto diols, respectively, in fair to good yield.These products result from S-O cleavage of the sultone ring.Primary sultones and α-dialkyl-β'-hydroxy γ-sultones give predominantly C-O cleavage to form sulfonic acid derivatives. β-Sultones are much less reactive toward the mixed hydride, and refluxing in dioxane is required for their reduction.