62170-25-6

Upstream product

• 100-66-3 methoxybenzene 
• 111-64-8 n-octanoic acid chloride 
• 124-07-2 Octanoic acid 
• 623-66-5 octanoic acid anhydride 
• 1119-90-0 di-n-butylzinc 
• 215667-87-1 4-iodo-1-(4-methoxyphenyl)-1-butanone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 124-13-0 Octanal 
• 693-04-9 butyl magnesium bromide 
• 623-12-1 4-chloromethoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 629-05-0 n-octyne 
• 696-62-8 para-iodoanisole 
• 502-49-8 cycloactanone 

Downstream Products

• 1370521-18-8 (Z)-4-methoxy-2-(methoxymethoxy)-1-[1-(4-methoxyphenyl)oct-1-en-1-yl]benzene 
• 1370521-20-2 (Z)-4-methoxy-1-[1-(4-methoxyphenyl)oct-1-en-1-yl]-2-nitrobenzene 
• 1806-26-4 p-Octylphenol 

Relevant academic research and scientific papers

Scope and Mechanism of the Redox-Active 1,2-Benzoquinone Enabled Ruthenium-Catalyzed Deaminative α-Alkylation of Ketones with Amines

The catalytic system formed in situ from the reaction of a cationic Ru-H complex with 3,4,5,6-tetrachloro-1,2-benzoquinone was found to mediate a regioselective deaminative coupling reaction of ketones with amines to form the α-alkylated ketone products. Both benzylic and aliphatic primary amines were found to be suitable substrates for the coupling reaction with ketones in forming the α-alkylated ketone products. The coupling reaction of PhCOCD3 with 4-methoxybenzylamine showed an extensive H/D exchange on both α-CH2 (41% D) and β-CH2 (21%) positions on the alkylation product. The Hammett plot obtained from the reaction of acetophenone with para-substituted benzylamines p-X-C6H4CH2NH2 (X = OMe, Me, H, F, Cl, CF3) showed a strong promotional effect by the amine substrates with electron-releasing groups (ρ = -0.49 ± 0.1). The most significant carbon isotope effect was observed on the α-carbon of the alkylation product (Cα = 1.020) from the coupling reaction of acetophenone with 4-methoxybenzylamine. The kinetics of the alkylation reaction from an isolated imine substrate led to the empirical rate law: rate = k[Ru][imine]. A catalytically active Ru-catecholate complex was synthesized from the reaction of the cationic Ru-H complex with 3,5-di-tert-butyl-1,2-benzoquinone and PCy3. The DFT computational study was performed on the alkylation reaction, which revealed a stepwise mechanism of the [1,3]-carbon migration step via the formation of a Ru(IV)-alkyl species with a moderate energy of activation (ΔG? = 32-42 kcal/mol). A plausible mechanism of the catalytic alkylation reaction via an intramolecular [1,3]-alkyl migration of an Ru-enamine intermediate has been compiled on the basis of these experimental and computational data.

Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(i) complexes

We have investigated the role of ring sizes and substituents in NHC ligands in some (NHC)Au(i) complexes in the hydration of internal alkynes. Despite the fact that using (NHC)Au(i) complexes in the hydration of diarylacetylenes leads to Markovnikov-type products, the precise tuning of ligands allows changing the regioselectivity in arylalkylacetylene hydration to the anti-Markovnikov-type.

Acylation of anisole with carboxylic acids catalyzed by tungsten oxide supported on titanium dioxide

Friedel-Crafts (F-C) acylation of anisole with octanoic acid was carried out on tungsten oxide (WO3) supported on various types of oxide supports. We have found that the highest activity was obtained when TiO2 was used as the support. WO3/TiO2 was found to be active in the acylation of anisole with carboxylic acids of varying alkyl chain lengths (C6–C10). It was possible to recycle the WO3/TiO2 catalyst for up to 5 times without deactivation. The turnover frequency (TOF) of the catalyst was closely correlated with the electronegativity of the cation of the support used for WO3. When a strong basic oxide such as CeO2 was used as a support, the acid strength of WO3 was diminished, while the strong acidity of WO3 was retained on a weak basic support like TiO2. This explains why the acid strength and consequently, the activity, were found to be the highest for the WO3/TiO2 catalyst. The trend of the catalytic performance was consistent with the order of acid strength of WO3 on different supports measured by temperature-programmed desorption of NH3.

Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols

We report herein the development of a S atom transfer process using triethyl phosphite as the S atom acceptor that allows thiols to serve as precursors of C-centered radicals. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups readily participate in this reductive coupling. This process is driven by the exchange of relatively weak S-H and C-S bonds of aliphatic thiols for C-H, C-C, and S-P bonds of the products formed.

Ketide compounds, method for manufacturing, and use for treating diabetes thereof

The present invention relates to ketide compounds, as well as ketide compounds. The present invention relates to a method for preparing a ketide compound, and a use thereof, in which various anti-diabetic TMPA derivative designs can be induced, and is effective in comparison with existing multi-stage synthesis. In addition, the ketide compounds according to the present invention have strong AMPMPK activity and are expected to be useful as a therapeutic agent for diabetes. (by machine translation)

Iron(III)-Catalyzed Hydration of Unactivated Internal Alkynes in Weak Acidic Medium, under Lewis Acid-Assisted Br?nsted Acid Catalysis

Alkylarylalkynes are converted with full regioselectivity into the corresponding arylketones by formal hydration of the triple bond under weak acidic conditions, at times and temperatures (≤95 °C) comparable to those used for terminal alkynes. The process catalyzed by Fe2(SO4)3nH2O in glacial acetic acid exhibits good functional group compatibility, including that with bulky triple bond substituents, and can be extended to the one-pot transformation of aryltrimethylsilylacetylenes into acetyl derivatives via a desilylation-hydration sequence. The overall reactivity pattern along with proton affinity data indicate that the triple bond is activated by proton transfer rather than by π-interaction with the metal ion. This mechanistic feature, at variance with that of noble metal catalysts, accounts for the total regioselectivity and the insensitivity to steric hindrance exhibited by the Fe2(SO4)3nH2O/AcOH catalytic system. (Figure presented.).

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.

Palladium-catalyzed room temperature acylative cross-coupling of activated amides with trialkylboranes

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids

Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an inexpensive palladium catalyst to generate the key alkyl radical intermediate. These mild conditions enabled the synthesis of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone.

Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds

We report a new photocatalytic protocol for the redox-neutral isomerization of cyclic alcohols to linear ketones via C-C bond scission. Mechanistic studies demonstrate that key alkoxy radical intermediates in this reaction are generated via the direct homolytic activation of alcohol O-H bonds in an unusual intramolecular PCET process, wherein the electron travels to a proximal radical cation in concert with proton transfer to a weak Br?nsted base. Effective bond strength considerations are shown to accurately forecast the feasibility of alkoxy radical generation with a given oxidant/base pair.