86457-70-7

Upstream product

• 2181-42-2 trimethylsulphonium iodide 
• 529-20-4 2-methylphenyl aldehyde 
• 1774-47-6 trimethylsulfoxonium iodide 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 333-27-7 methyl trifluoromethanesulfonate 
• 2181-44-4 trimethylsulfonium methylsulfate 
• 119391-23-0 C₁₆H₁₇N₂O₃S^(1-)*Na⁽¹⁺⁾ 
• 6814-64-8 methylenedimethyl sulfurane 
• 593-71-5 Chloroiodomethane 

Downstream Products

• 77969-29-0 2-[2-(2-Chloro-3,4-dimethoxy-phenyl)-ethylamino]-1-o-tolyl-ethanol 
• 1323143-09-4 C₉H₉⁽²⁾HO 
• 10166-08-2 2-methyl-benzeneacetaldehyde 
• 577-16-2 2-Methylacetophenone 
• 5033-67-0 2-(2-methylphenyl)-1-phenyl-1-ethanone 
• 92876-67-0 1-(2-methylphenyl)ethane-1,2-diol 
• 1403603-11-1 N,N‐dimethyl‐2‐oxo‐2‐(o‐tolyl)acetamide 
• 139458-89-2 2-(2-methylphenyl)thiirane 

Relevant academic research and scientific papers

Kinetic resolution ofN-aryl β-amino alcoholsviaasymmetric aminations of anilines

An efficient kinetic resolution ofN-aryl β-amino alcohols has been developedviaasymmetricpara-aminations of anilines with azodicarboxylates enabled by chiral phosphoric acid catalysis. Broad substrate scope and high kinetic resolution performances were afforded with this method. Control experiments supported the critical roles of the NH and OH group in these reactions.

MeOTf/KI-catalyzed efficient synthesis of 2-arylnaphthalenesviacyclodimerization of styrene oxides

The MeOTf/KI-catalyzed synthesis of 2-arylnaphthalene derivatives from aryl ethylene oxides in alcohol under ambient conditions is described. The present protocol has a higher atom efficiency and wider substrate applicability with excellent yields. The reaction proceeded using the aryl ethylene oxides to give 2-arylnaphthalenes either in homo-coupling or in cross-coupling. The reaction could also be carried out at the gram scale in minutes.

MeOTf-catalyzed formal [4?+?2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion

MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.

Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).

Pyrazine dicarboxylate-bridged arsenotungstate: Synthesis, characterization, and catalytic activities in epoxidation of olefins and oxidation of alcohols

A praseodymium(iii)-containing arsenotungstate K16H15Li7[Pr2(H2O)3(pzdc)As3W29O103]2·38H2O (1) (pzdc = pyrazine-2,3-dicarboxylic acid) was synthesized by a conventional aqueous solution method and characterized by elemental analysis, IR spectroscopy, thermogravimetric analysis (TGA), powder X-ray diffraction (PXRD), and single crystal X-ray diffraction. Structural analysis revealed that compound 1 was constructed by two identical subunits {Pr2(H2O)3(AsW9O33)3W2O4} bridged together by two pzdc ligands. In addition, compound 1 could act as an efficient catalyst for the epoxidation of olefins and oxidation of alcohols with hydrogen peroxide (H2O2) as the oxidant. In particular, the turnover frequency (TOF) in the oxidation of 1-phenylethanol reached up to 10170 h-1, which is higher than that of previously reported catalysts.

Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants

Cytochrome P450 CYP102A1 (P450 Bm3) variants were used to investigate the products arising from the P450 catalysed oxidation of a range of disubstituted benzenes. The variants used all generated increased levels of metabolites compared to the wild-type enzyme. With ortho-halotoluenes up to six different metabolites could be identified whereas the oxidation of 2-methoxytoluene generated only two aromatic oxidation products. Addition of an ethyl group markedly shifted the selectivity for oxidation to the more reactive benzylic position. Epoxidation of an alkene was also preferred to aromatic oxidation in 2-methylstyrene. Significant minor products arising from the migration of one substituent to a different position on the benzene ring were formed during certain P450-catalysed substrate turnovers. For example, 2-bromo-6-methylphenol was formed from the turnover of 2-bromotoluene and the dearomatisation product 6-ethyl-6-methylcyclohex-2,4-dienone was generated from the oxidation of 2-ethyltoluene. The RLYF/A330P variant altered the product distribution enabling the generation of certain metabolites in higher quantities. Using this variant produced 4-methyl-2-ethylphenol from 3-ethyltoluene with ≥90 % selectivity and with a biocatalytic activity suitable for scale-up of the reaction.

Three powerful dinuclear metal-organic catalysts for converting CO2 into organic carbonates

Developing efficient catalysts for converting carbon dioxide (CO2) into varied organic carbonates is an important scientific goal. By using the NH2-functionalized tripodal ligand 2-((bis(2-aminoethyl)amino)methyl)phenol (HL), three dinuclear metal-organic complexes [Zn(L)]2·2ClO4 (1), [Cu(L)]2·2ClO4·2H2O (2) and [Cd(L)]2·2ClO4 (3) have been successfully isolated and structurally characterized using single-crystal X-ray diffraction analyses. Considering the dinuclear metal centers and the NH2-functional groups in the structures, 1-3 were investigated as catalysts for converting CO2 into organic carbonates, and the results show that 1-3 exhibit an outstanding ability for converting CO2 into varied organic carbonates at atmospheric pressure (0.1 MPa). The catalytic system also displays a wide substrate scope and high catalytic activity, and the reaction mechanism has been proposed herein.

Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles and epoxides: Regioselective synthesis of substituted 3,4-dihydro-2 H-1,4-oxazines

Rhodium-catalyzed transannulation of 1,2,3-triazoles and ring-opening reactions of epoxides is described. A number of 3,4-dihydro-2H-1,4-oxazines are obtained in moderate yields probably involving generation of α-imino rhodium(II) carbene species.

Nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids

Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates C-C bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X-ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving C sp 3-O bond activation. A variety of α-substituted alcohols were generated with good reaction efficiency by a multicatalytic sequence. Copyright

Catalytic (asymmetric) methylene transfer to aldehydes

[Chemical equation presented] An investigation Into the poor activity of sulfides as catalysts for sulfonium-ylide-mediated methylene transfer to aldehydes has indicated that ylide formation is the problematic catalytic cycle step. Alkylation with traditional electrophiles does not proceed with sufficient efficiency to allow the sulfide to be used catalytically. Methyl triflate rapidly alkylates cyclic thiolanes under mild conditions, allowing their use in efficient aldehyde epoxidation reactions (in conjunction with phosphazene bases) at loadings as low as 10 mol %.