60507-03-1

Upstream product

• 98-86-2 acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 4079-52-1 methoxymethyl phenyl ketone 
• 22034-19-1 deuterio(dimethyl)phenylsilane 
• 4747-13-1 α-methoxystyrene 
• 17537-31-4 Acetophenone-methyl-d3 
• 52881-58-0 2-deuterio-2-phenyloxirane 
• 1193-80-2 α-deuteriostyrene 
• 15480-89-4 potassium enolate of acetophenone 
• 23088-41-7 1-phenylethyl-1-d₁ bromide 
• 100-42-5 styrene 
• 3101-96-0 1-deuterio-1-phenylethanol 
• 721-04-0 2-phenoxy-1-phenylethanone 

Downstream Products

• 74636-51-4 2,2-dideuterioacetophenone 
• 98-86-2 acetophenone 
• 1220985-73-8 (E)-N'-(1-(3-methoxyphenyl)ethylidene)-4-methylbenzenesulfonohydrazide-d1 

Relevant academic research and scientific papers

Mechanistic Difference in Photoreduction of Phenacyl Halides by NADH Model Compounds

Photoreduction of phenacyl halides by an NADH model compound, 10-methylacridan (AcrH2), in MeCN proceeds via photoinduced electron transfer from the singlet excited state of AcrH2 to phenacyl halides without the conribution of radical chain reactions, while the photoreduction by another NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH), proceeds via photoinduced radical chain reactions.The origin of the mechanistic difference between AcrH2 and BNAH has been discussed.

Palladium-catalyzed conjugate reduction of enones into α,β- dideuterioketones with hexamethyldisilane and deuterium oxide

Conjugated enones are reduced by readily available Me 3SiSiMe3 and D2O in the presence of a catalytic amount of [PdCl(η3-C3H5)] 2-PPh3 to give α,β-dideuterioketones. The Royal Society of Chemistry.

Synthesis method of alpha or beta-substituted aromatic ketone

The invention discloses a synthesis method of alpha-or beta-substituted aromatic ketone. The method comprises the following steps: under the condition of inert gas, reacting alpha-oxo-aryl ethanone compounds, B2pin2, PDI-CoCl2 and MBHEt3 in an organic solvent at room temperature, then adding a compound 2, and continuously reacting to obtain a compound 3, wherein in the MBHEt3, M is an alkali metal; the compound 2 is selected from the group consisting of deuterated methanol, Selectfluoro, a TogniII reagent or R2CHO; R2 is an aromatic substituent or alkyl; the organic solvent is an aprotic organic solvent. According to the method, the alpha-oxo aryl ethanone is used as a raw material, a cheap and stable boron reagent and an efficient cobalt catalyst which is cheap and easy to obtain are used, an activating reagent MBHEt3 is added to generate an enol boron ether intermediate, then the enol boron ether intermediate and different electrophilic reagents are synthesized into alpha-or beta-substituted aromatic ketone, the reaction is carried out at normal temperature, and the operation is convenient.

Catalytic Enantioselective Direct Aldol Addition of Aryl Ketones to α-Fluorinated Ketones

The catalytic enantioselective synthesis of α-fluorinated chiral tertiary alcohols from (hetero)aryl methyl ketones is described. The use of a bifunctional iminophosphorane (BIMP) superbase was found to facilitate direct aldol addition by providing the strong Br?nsted basicity required for rapid aryl enolate formation. The new synthetic protocol is easy to perform and tolerates a broad range of functionalities and heterocycles with high enantioselectivity (up to >99:1 e.r.). Multi-gram scalability has been demonstrated along with catalyst recovery and recycling. 1H NMR studies identified a 1400-fold rate enhancement under BIMP catalysis, compared to the prior state-of-the-art catalytic system. The utility of the aldol products has been highlighted with the synthesis of various enantioenriched building blocks and heterocycles, including 1,3-aminoalcohol, 1,3-diol, oxetane, and isoxazoline derivatives.

Water-Accelerated Nickel-Catalyzed α-Crotylation of Simple Ketones with 1,3-Butadiene under pH and Redox-Neutral Conditions

We report a nickel/NHC-catalyzed branched-selective α-crotylation of simple ketones using 1,3-butadiene as the alkylation agent. This reaction is regioselective and operated under pH and redox-neutral conditions. Water was used as the sole additive, which significantly accelerates the transformation.

Nucleophilic Isomerization of Epoxides by Pincer-Rhodium Catalysts: Activity Increase and Mechanistic Insights

Herein, we present the efficient isomerization of epoxides into methyl ketones with a novel pincer-rhodium complex under very mild conditions. The catalyst system has an excellent functional group tolerance and a wide array of epoxides was tested. The corresponding methyl ketones were obtained in very high yields with excellent chemo- and regioselectivity. In addition, we investigated mechanistic details like the isomerization of the catalyst, and we obtained evidence that the catalytic cycle follows a β-hydride elimination-reductive elimination pathway after the nucleophilic ring opening of the epoxide.

Self-hydrogen transfer hydrogenolysis of β-O-4 linkages in lignin catalyzed by MIL-100(Fe) supported Pd-Ni BMNPs

A MIL-100(Fe) supported Pd-Ni BMNP catalyst has been fabricated, and the catalyst exhibits superior catalytic performance toward the intramolecular transfer hydrogenolysis of lignin model compounds and organosolv lignin. Alcoholic groups (CαH-OH) of lignin were exploited as the hydrogen source, and selective cleavage of β-O-4 linkages in lignin was realized without an extra hydrogen donor. This protocol was suitable for organosolv lignin as well as model compounds; several phenols and functionalized acetophenones were detected when extracted lignin was treated in our system. The catalyst exhibits outstanding catalytic stability during the reaction process, which can be ascribed to the porous structure and the strong water stability of MIL-100(Fe). The excellent catalytic performance of Pd1Ni4/MIL-100(Fe) highlights the "synergistic effect" between the BMNPs and the functional synergy between MNPs and MOFs, and our work shows the bright future of BMNPs and MOFs in the development of catalysts for sustainable chemistry.

Mechanism of Catalytic Oxidation of Styrenes with Hydrogen Peroxide in the Presence of Cationic Palladium(II) Complexes

Kinetic studies, isotope labeling, and in situ high-resolution mass spectrometry are used to elucidate the mechanism for the catalytic oxidation of styrenes using aqueous hydrogen peroxide (H2O2) and the cationic palladium(II) compound, [(PBO)Pd(NCMe)2][OTf]2 (PBO = 2-(pyridin-2-yl)benzoxazole). Previous studies have shown that this reaction yields acetophenones with high selectivity. We find that H2O2 binds to Pd(II) followed by styrene binding to generate a Pd-alkylperoxide that liberates acetophenone by at least two competitive processes, one of which involves a palladium enolate intermediate that has not been previously observed in olefin oxidation reactions. We suggest that acetophenone is formed from the palladium enolate intermediate by protonation from H2O2. We replaced hydrogen peroxide with t-butyl hydroperoxide and found that, although the palladium enolate intermediate was observed, it was not on the major product-generating pathway, indicating that the form of the oxidant plays a key role in the reaction mechanism.

A stable N-heterocyclic carbene organocatalyst for hydrogen/deuterium exchange reactions between pseudoacids and deuterated chloroform

It was observed that the stable and commercially available N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, the so-called IDipp, catalyzes hydrogen/deuterium exchange reactions between pseudoacids and chloroform-d1

Gated access to α-lithiated phenyltetrahydrofuran: Functionalisation via direct lithiation of the parent oxygen heterocycle

Cycloreversion of α-lithiated phenyltetrahydrofuran was successfully tamed at -78 °C in a non-coordinating solvent in the presence of TMEDA. This anion showed excellent nucleophilicity and could be intercepted with a variety of structurally different electrophiles to give 2,2-disubstituted derivatives which can be further elaborated to γ-butyrolactones. The Royal Society of Chemistry 2013.