40950-94-5

Upstream product

• 95-50-1 1,2-dichloro-benzene 
• 140-88-5 ethyl acrylate 
• 64-17-5 ethanol 
• 141-82-2 malonic acid 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 51-44-5 3,4-dichlorbenzoic acid 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 3024-72-4 3,4-dichlorobenzoyl chloride 
• 7312-27-8 3,4-Dichlorocinnamic acid 
• 1202-39-7 3,4-dichlorocinnamic acid 
• 75-03-6 ethyl iodide 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 17437-51-3 N-(ethoxycarbonyl)triphenylphosphinimine 

Downstream Products

• 7116-47-4 ethyl 3-(3,4-dichlorophenyl)propanoate 
• 56984-70-4 3-(3,4-dichlorophenyl) prop-2-en-1-ol 
• 99184-26-6 2-amino-6-(3,4-dichloro-phenyl)-5,6-dihydro-3H-pyrimidin-4-one 
• 63429-36-7 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3,4-dichlorobenzyl)-4-pyrimidone dihydrochloride 
• 63204-34-2 5-(3,4-dichloro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 63204-35-3 5-(3,4-dichlorobenzyl)-2-methylthio-4-pyrimidone 
• 1432059-42-1 (R,E)-tert-butyl {3-cyano-1-[3-(3,4-dichlorophenyl)allyl]-2-oxoindolin-3-yl}carbamate 
• 1432059-19-2 C₂₂H₂₀Cl₂N₂O₃ 
• 1432059-82-9 tert-butyl (E)-(3-cyano-1-(3-(3,4-dichlorophenyl)allyl)-2-oxoindolin-3-yl)carbamate 
• 148775-22-8 3-(3,4-dichlorophenyl)-prop-2-en-1-ol 
• 149946-25-8 (E)-4-(3-bromoprop-1-en-1-yl)-1,2-dichlorobenzene 

Relevant academic research and scientific papers

Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole

A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.

Ternary Catalysis Enabled Three-Component Asymmetric Allylic Alkylation as a Concise Track to Chiral α,α-Disubstituted Ketones

Multicomponent reactions that involve interception of onium ylides through Aldol, Mannich, and Michael addition with corresponding bench-stable acceptors have demonstrated broad applications in synthetic chemistry. However, because of the high reactivity and transient survival of these in situ generated intermediates, the substitution-type interception process, especially the asymmetric catalytic version, remains hitherto unknown. Herein, a three-component asymmetric allylation of α-diazo carbonyl compounds with alcohols and allyl carbonates is disclosed by employing a ternary cooperative catalysis of achiral Pd-complex, Rh2(OAc)4, and chiral phosphoric acid CPA. This method represents the first example of three-component asymmetric allylic alkylation through an SN1-type trapping process, which involves a convergent assembly of two active intermediates, Pd-allyl species, and enol derived from onium ylides, providing an expeditious access to chiral α,α-disubstituted ketones in good to high yields with high to excellent enantioselectivity. Combined experimental and computational studies have shed light on the mechanism of this novel three-component reaction, including the critical role of Xantphos ligand and the origin of enantioselectivity.

Dual Ligand-Enabled Nondirected C?H Olefination of Arenes

The application of the Pd-catalyzed oxidative C?H olefination of arenes, also known as the Fujiwara–Moritani reaction, has traditionally been limited by the requirement for directing groups on the substrate or the need to use the arene in large excess, ty

Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity

In the presence of a neutral dppf-modified iridium catalyst and Cs2CO3, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate-directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine.

S,O-Ligand-Promoted Palladium-Catalyzed C-H Functionalization Reactions of Nondirected Arenes

Pd(II)-catalyzed C-H functionalization of nondirected arenes has been realized using an inexpensive and easily accessible type of bidentate S,O-ligand. The catalytic system shows high efficiency in the C-H olefination reaction of electron-rich and electron-poor arenes. This methodology is operationally simple, scalable, and can be used in late-stage functionalization of complex molecules. The broad applicability of this catalyst has been showcased in other transformations such as Pd(II)-catalyzed C-H acetoxylation and allylation reactions.

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.

Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base

A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.

Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates

Enantioselective allylic substitution with enolates derived from aliphatic esters under mild conditions remains challenging. Herein we report iridium-catalyzed enantioselective allylation reactions of silyl ketene acetals, the silicon enolates of esters, to form products containing a quaternary carbon atom at the nucleophile moiety and a tertiary carbon atom at the electrophile moiety. Under relatively neutral conditions, the allylated aliphatic esters were obtained with excellent regioselectivity and enantioselectivity. These products were readily converted into primary alcohols, carboxylic acids, amides, isocyanates, and carbamates, as well as tetrahydrofuran and γ-butyrolactone derivatives, without erosion of enantiomeric purity.

Solvent-free, one-pot synthesis of α,β-unsaturated esters in the presence of a C3-symmetric arsine

An efficient synthesis of α, β-unsaturated esters is achieved via a one-pot reaction in the presence of a C3-symmetric arsine. The key advantages are the short reaction time, simple workup, mild reaction conditions, and high yields.

Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions

A polyethyleneimine-supported triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene product in situ. In these transformations, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for activating trichlorosilane in the subsequent reduction reaction.