92576-43-7

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 30018-16-7 (1-ethoxycarbonylethyl)triphenylphosphonium bromide 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 80-62-6 methacrylic acid methyl ester 
• 535-11-5 Ethyl 2-bromopropionate 
• 77902-90-0 rac-2-(Trifluormethylsulfonyloxy)propionsaeure-ethylester 
• 64-17-5 ethanol 
• 1202-60-4 -2-methyl-3-(4-chlorophenyl)prop-2-enoic acid 

Downstream Products

• 1202-60-4 -2-methyl-3-(4-chlorophenyl)prop-2-enoic acid 
• 24654-54-4 3-(4-chlorophenyl)-2-methylpropenal 
• 1228457-66-6 C₂₄H₃₄ClNO₄Si 
• 1228457-55-3 C₁₇H₂₄ClNOSi 
• 1351464-68-0 C₁₅H₁₉ClO₂ 
• 103305-31-3 (E)-3-(4-Chlorophenyl)-2-methylprop-2-en-1-ol 

Relevant academic research and scientific papers

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes

The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.

Asymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co–Catalyzed, Enantioselective Proton-Transfer

We report an enantioselective Nazarov cyclization catalyzed by chiral hydrogen-bond-donors in concert with silyl Lewis acids. The developed transformation provides access to tri-substituted cyclopentenones in high levels of enantioselectivity (up to 95% e.e.) from a variety of simple unactivated dienones. Kinetic and mechanistic studies are consistent with a reversible 4π-electrocyclization C?C bond-forming step followed by rate- and enantio-determining proton-transfer as the mode of catalysis. (Figure presented.).

Aryltriolborates as air- and water-stable bases for wittig olefination

Tetrabutylammonium aryltriolborates have been synthesized in 37-66% yield by a one-pot procedure from arylboronic acids, 1,1,1-tris(hydroxymethyl)ethane, and aqueous tetrabutylammonium hydroxide. The aryltriolborates can be used as bases in Wittig reactions of aromatic aldehydes with all three types of phosphorus ylides: stabilized and semistabilized ylides can be generated at room temperature, and nonstabilized ylides at 120 °C (bath temperature).

Highly enantioselective hydrogenation of 2-substituted-2-alkenols catalysed by a ChenPhos-Rh complex

Highly enantioselective hydrogenation of a variety of 2-substituted-2- alkenols has been achieved using a ChenPhos-Rh complex as catalyst, giving ≥99% ee for most substrates. Optically active antifungal agent amorolfine was first synthesised using hydrogenation as the key step. This journal is

Arenediazonium salts immobilized in imidazolium ionic liquids as electrophilic partners in the Pd(OAc)2-catalyzed Matsuda-Heck arylation

The utility of arenediazonium salts immobilized in imidazolium-ILs [BMIMPF6 and BMIMBF4] for facile, high yielding, synthesis of olefins via the Pd(OAc)2-catalyzed Matsuda-Heck arylation reaction has been demonstrated. The reaction can also be performed as a two-step process in the IL starting from ArNH2, by sequential in-situ diazotization-arylation. Simple product isolation and the recycling/re-use of the IL are additional advantages of this one-pot method.

Chromatography-free wittig reactions using a bifunctional polymeric reagent

The first example of a polystyrene bearing two distinct reagent groups has been prepared. This phosphine and amine functionalized material was used in one-pot Wittig reactions with an aldehyde and either an α-halo-ester, -ketone, or -amide. Due to the heterogeneous nature of the polymer, the desired alkene product of these reactions could be isolated in excellent yield in essentially pure form after only filtration and solvent removal.

Synthesis and characterization of pentaerythritol-derived oligoglycol and their application to catalytic Wittig-type reactions

Several pentaerythritol-derived oligoglycols 1 with free hydroxyl groups are readily prepared by a convergent approach. Quantitative 13C NMR proves to be an efficient tool for the characterization of oligoglycols. The corresponding telluride of oligoglycol 17 is synthesized and used as a good catalyst for Wittig-type reactions in preparing both disubstituted and trisubstituted olefins in good to high yields.

Kinetic study of microwave-assisted Wittig reaction of stabilised ylides with aromatic aldehydes

The Wittig reaction of a pool of stabilised ylides and aromatic aldehydes was carried out in a microwave oven. Only a few minutes were needed for high conversion rates under microwave heating in comparison to hour time with traditional methods.

Activated Alumina Promoted Stereoselective Wittig Reaction

Aldehydes undergo efficient E-stereoselective Wittig olefination with alkylidenetriphenylphosphoranes in the presence of activated alumina under mild conditions with high yields.