23204-80-0

Upstream product

• 15424-05-2 6-bromo-5,5-dimethyl-1-hexene 
• 587-04-2 m-Chlorobenzaldehyde 
• 96-22-0 pentan-3-one 
• 108-37-2 1-bromo-3-chlorobenzene 
• 625-99-0 3-iodochlorobenzene 
• 3840-17-3 1-allyl-3-chlorobenzene 
• 2039-85-2 3-Chlorostyrene 
• 917-54-4 methyllithium 
• 106175-53-5 C₉H₈ClLi 
• 507-19-7 t-butyl bromide 

Downstream Products

• 105643-18-3 1-(m-chlorophenyl)allyl acetate 
• 105643-17-2 3-chlorocinnamyl acetate 

Relevant academic research and scientific papers

Method for synthesizing alkyl olefin through coupling of double-bond carbon-hydrogen bond and saturated carbon-hydrogen bond

The invention discloses a method for synthesizing alkyl olefin through coupling of a double-bond carbon-hydrogen bond and a saturated carbon-hydrogen bond. According to to the method, one-pot reactionis implemented on olefin and sulfoxide in the presence of ferric salt and hydrogen peroxide to generate alkyl olefin; in the method, sulfoxide is simultaneously used as a hydrocarbylation reagent anda solvent of olefin, and a reaction product is alkyl olefin from sulfoxide alkyl coupled with olefin carbon atoms, so that an olefin carbon chain is increased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.

Method for synthesizing 1, 2-disubstituted olefin through reaction of terminal group olefin and sulfoxide

The invention discloses a method for synthesizing 1, 2-disubstituted olefin by reaction of terminal olefin and sulfoxide. According to the method, terminal olefin with sulfoxide make reaction in one pot in the presence of ferric salt and hydrogen peroxide to generate the 1, 2-disubstituted olefin. sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefin, and a reaction product is 1, 2-disubstituted olefin of which a terminal carbon atom in terminal olefin is coupled with a sulfoxide alkyl group, so that an olefin carbon chain is increased; the reaction conditionsare mild, the selectivity is high, the yield is high, and industrial production is facilitated.

Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions

We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.

Method for synthesizing (E)-Anethol and Related Compounds By Cross Coupling Reaction of Potassium alllyltrifluroborate and 4-bromoanisole and aryl halides

Methods of producing substituted and non-substituted beta-methyl styrene by a cross-coupling reaction are provided. The disclosure also provides for methods of preparing (E)-Anethol and related compounds by a cross coupling reaction of potassium allyltrifluoroborate and 4-bromoanisole and aryl halides. Compounds, compositions, and methods of treating disorders utilizing beta-methyl styrene are also provided.

Efficient double bond migration of allylbenzenes catalyzed by Pd(OAc) 2-HFIP system with unique substituent effect

A novel catalyst system of Pd(OAc)2-HFIP induces double-bond migration of allylbenzenes under mild conditions with low catalytic loading to afford 1-propenylbenzenes. The reaction shows a unique substituent effect that is highly dependent on the distance of substituents from the allylic moiety. Thus, the reactivity of substrates bearing a methyl group is ordered in para > meta > ortho, whereas it is entirely reversed as ortho > meta > para for methoxy and chloro substituents.

Remarkable regioselectivity in microwave-enhanced palladium-catalyzed allylation reaction involving allyltrifluoroborates and aryl halides

An unprecedented cross-coupling reaction of potassium allyltrifluoroborates and aryl halides to the corresponding trans-β-methylstyrenes in the presence of PdCl2(dtbpf) catalyst under microwave heating was developed.

A tandem Aldol-Grob reaction of ketones with aromatic aldehydes

Aromatic aldehydes react with ketones to produce (E)-1-aryl-1-alkenesvia a tandem Aldol-Grob cleavage reaction sequence. The reaction, initiated by boron trifluoride, also produces a carboxylic acid fragment.

Mechanistic aspects of aminium salt-catalyzed Diels-Alder reactions: The substrate ionization step

Substituent effects in the aminium salt catalyzed Diels-Alder reactions of 2,3-dimetnyl-1,3-butadiene with a series of meta and para substituted β-methylstyrenes are used to probe detailed mechanistic aspects of these reactions. Kinetic studies were carried out using two different aminium salt catalysts and also electrochemically, using anodic potentials corresponding to the oxidation potentials of the aminium salts. Substituent effects in the equilibrium oxidations of the styrene substrates to the corresponding cation radicals were also studied, via oxidation potential measurements. The results indicate rate determining one electron oxidation of the sytrenes to their cation radicals via an outer sphere electron transfer.

Protonation and Alkykation of 1-Arylpropenyl-lithium

The protonation and alkylation of 1-arylpropenyl-lithium (1a-c) in ether was undertaken systematically; the regio- and stereo-chemistry being influenced by various factors.The characteristic features are as follows. (a) Protonation occurs predominantly at C-3, whereas the sterically more crowded C-1 is the more favoured site for alkylation, and (b) although 1-arylpropenyl-lithium (1) seems to exist mainly as the E-isomer, in some cases the product (3) or (5) having the Z-configuration is produced from attack at C-3 in a significant amount together with the E-isomer, e.g. protonation by oxygen acids in the presence or absence of tetramethylethylenediamine and methylation of the p-methoxy derivative (1a).

Reaction of Phenyl-Substituted Allyllithiums with tert-Alkyl Bromides. Remarkable Difference in the Alkylation Regiochemistry between a Polar Process and the One Involving Single-Electron Transfer

The reaction of phenyl-substituted allyllithiums 1a-h with tert-alkyl bromides was investigated systematically.The alkylation regiochemistry was influenced in a complicated fashion by various factors including substituent effects, both steric and electronic, solvents, and the presence of strongly coordinating additives, tetramethylethylenediamine and hexamethylphosphoramide.On the basis of the cyclizable probe experiments, the observed regiochemistry was interpreted as follows. (a) The reaction proceeds by two alternative pathways, a polar one and single electron transfer (SET), the extent of each path being influenced by the variable factors and (b) a polar pathway favors coupling at the phenyl-substituted site (C-1), while in the case of SET the C-C bond formation occurs predominantly at the site far from the phenyl substituent (C-3).