100765-45-5

Upstream product

• 103-13-9 1-(4-methoxyphenyl)-4-methyl-1-penten-3-one 
• 625-81-0 diisopropyl zinc 
• 683226-13-3 3-(4-methoxyphenyl)-thiopropionic acid (S)-dodecyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 1346656-92-5 S-phenyl 3-(4-methoxyphenyl)propanethioate 
• 77047-87-1 isopropyl zinc bromide 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 1146977-84-5 4-methoxybenzyl 4-methyl-3-oxopentanoate 
• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 
• 73086-84-7 1-isopropyl-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt 
• 75-26-3 isopropyl bromide 
• 208453-06-9 3-(4-methoxyphenyl)propionic acid ethanethiol ester 
• 75-30-9 2-iodo-propane 
• 870-63-3 prenyl bromide 

Downstream Products

• 646039-09-0 1-(4-methoxyphenyl)-4-methylpentan-3-one (E)-oxime 

Relevant academic research and scientific papers

One-Pot Ketone Synthesis with Alkylzinc Halides Prepared from Alkyl Halides via a Single Electron Transfer (SET) Process: New Extension of Fukuyama Ketone Synthesis

One-pot ketone synthesis has been developed with in situ activation of alkyl halides to alkylzinc halides in the presence of thioesters and Pd-catalyst. The new method provides us with a reliable option for a coupling at a late stage in a convergent synth

A novel procedure for the synthesis of multifunctional ketones through the Fukuyama coupling reaction employing dialkylzincs

Treatment of thiol esters 1 with dialkylzincs 2 in the presence of zinc bromide, that was in situ prepared from zinc dust and bromine, provided various functionalized ketones 3 in high yields. The reaction mechanism, which may shift the Schlenk equilibrium from dialkylzincs 2 to reactive alkylzinc bromide 5, was postulated to account for the facile coupling reaction.

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.

Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates

Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.

Pd-catalyzed Fukuyama cross-coupling of secondary organozinc reagents for the direct synthesis of unsymmetrical ketones

The coupling of acyl electrophiles with organometallic reagents represents a convergent route toward complex and versatile ketone products. Despite the mild conditions and high functional group tolerance, the cross-coupling of carboxylic acid derivatives,

Ni-catalyzed reductive coupling of alkyl acids with unactivated tertiary alkyl and glycosyl halides

This work highlights Ni-catalyzed reductive coupling of alkyl acids with alkyl halides, particularly sterically hindered unactivated tertiary alkyl bromides for the production of all carbon quaternary ketones. The reductive strategy is applicable to α-selective synthesis of saturated, fully oxygenated C-acyl glycosides through easy manipulations of the readily available sugar bromides and alkyl acids, avoiding otherwise difficult multistep conversions. Initial mechanistic studies suggest that a radical chain mechanism (cycle B, Scheme 1) may be plausible, wherein MgCl2 promotes the reduction of NiII complexes.

Enantiospecific bromonium ion generation and intramolecular capture: A model system for asymmetric bromonium ion-induced polyene cyclisations

Scalemic bromonium ions generated enantiospecifically by the action of catalytic triflic acid on scalemic regioisomeric bromohydrin derivatives are trapped intramolecularly, enantiospecifically and regioselectively to give bicyclic brominated carbocycles in excellent yield and high enantiomeric excess. This enantiospecific pathway is not significantly perturbed by the addition of a trisubstituted alkene.

Synthesis of Quinolines and 2H-Dihydropyrroles by Nucleophilic Substitution at the Nitrogen Atom of Oxime Derivatives

Isomerization of oxime derivatives was researched in detail to find out the methods for the syn-anti isomerization of O-substituted oximes. Based on these findings were developed simple methods for the preparation of aza-heterocycles from both stereoisomers of oximes. Quinolines were synthesized from β-aryl ketone oximes by treatment with trifluoroacetic anhydride and 4-chloranil. γ,δ-Unsaturated O-methoxyacetyloximes were transformed to 2H-dihydropyrroles by reaction with methoxy-acetic acid.

Friedel-Crafts Cyclialkylations of Some Epoxides. 3. Cyclizations of Tertiary and Meta-Substituted Arylalkyl Epoxides

The intramolecular cyclization of aryl groups to tertiary epoxide position was investigated, and the results were used to test the applicability of Baldwin's rules to this specific class of reactions.As a probe into mechanism of reactions studied earlier, the cyclizations of some meta-substituted 1,2-epoxy-5-phenylpentanes were examined to determine positional selectivities.The data obtained were compared with those of other studies, and comments are made on the reaction mechanism.