60341-39-1

Upstream product

• 13991-36-1 4-bromocrotonic acid 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 107-93-7 (E)-but-2-enoic acid 
• 84837-75-2 3-benzyl-3-(phenylthio)-propionic acid 
• 154457-63-3 1-(tert-butoxycarbonyl)-2-benzylethene 
• 87121-06-0 1,1-bis(trimethylsilyloxy)-buta-1,3-diene 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 122-78-1 phenylacetaldehyde 
• 631-64-1 dibromoacetic acid 
• 141-82-2 malonic acid 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 300-57-2 allylbenzene 
• 124-38-9 carbon dioxide 

Downstream Products

• 2243-53-0 styrylacetic acid 
• 137999-87-2 3-Acetylsulfanyl-4-phenyl-butyric Acid 
• 193549-13-2 3-(4-methoxyphenylsulfanyl)-4-phenylbutyric acid 
• 741280-85-3 (R)-N-(trans-4-phenylcrotonoyl)-4-phenyl-1,3-oxazolidin-2-one 
• 936620-77-8 C₂₂H₂₄O₂N₂ 
• 193549-14-3 N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramide 
• 137999-88-3 2-(1-Carboxymethyl-2-phenyl-ethylsulfanylmethyl)-hexanoic acid methyl ester 
• 137999-89-4 (S)-2-((R)-1-Benzyl-3-morpholin-4-yl-3-oxo-propylsulfanylmethyl)-hexanoic acid methyl ester 
• 24271-22-5 5-phenyl-2(E)-pentenoic acid 
• 63158-17-8 methyl (E)-4-phenyl-2-butenoate 
• 1146217-71-1 C₁₀H₉BrO₂ 
• 54966-42-6 ethyl 3-benzylacrylate 

Relevant academic research and scientific papers

Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide

A cuprous halide catalysed carboxylation of alkenyl boronic acids and alkenyl boronic acid pinacol esters under CO2, affording the corresponding α, β-unsaturated carboxylic acids in good yield, has been developed. The potassium (E)-trifluoro(styryl)borate is also compatible with this reaction. This simple and efficient copper(I) catalytic system showed good functional group tolerance.

Method for preparing alpha, beta-unsaturated carboxylic acid by reacting alkenyl boron compound with carbon dioxide under catalysis of cuprous halide

The invention discloses a method for preparing alpha, beta-unsaturated carboxylic acid through a carboxylation reaction of an alkenyl boron compound and carbon dioxide under the catalysis of cuprous halide. According to the method, carbon dioxide is used as a C1 source, the cuprous halide is adopted for catalysis, and alkoxide serves as alkali to react in an organic solvent, so the method is simple and easy to implement, has a wide substrate application range, converts various alkenyl boron compounds such as alkenyl boric acid, alkenyl borate and borate into corresponding alpha, beta-unsaturated carboxylic acid under mild conditions, and has a very high yield. The obtained product alpha, beta-unsaturated carboxylic acid is an important intermediate for preparing fine chemical products suchas perfumes, insecticides and the like.

Chiral integrated catalysts composed of bifunctional thiourea and arylboronic acid: Asymmetric aza-Michael addition of α,β-unsaturated carboxylic acids

The first intermolecular asymmetric Michael addition of nitrogen-nucleophiles to α,β-unsaturated carboxylic acids was achieved through a new type of arylboronic acid equipped with chiral aminothiourea. The use of BnONH2 as a nucleophile gives a range of enantioenriched β-(benzyloxy)amino acid derivatives in good yields and with high enantioselectivity (up to 90% yield, 97% enantiomeric excess (ee)). The obtained products are efficiently converted to optically active β-amino acid and 1,2-diamine derivatives.

Nickel-catalysed carboxylation of organoboronates

A nickel/N-heterocyclic carbene (NHC) catalysed carboxylation of aryl-, heteroaryl- and alkenylboronates, affording the corresponding carboxylic acids, has been developed. This transformation proceeds under one atmosphere of CO 2 with a broad range of substrates and exhibits good functional group compatibility. the Partner Organisations 2014.

Unravelling the olefin cross metathesis on solid support. Factors affecting the reaction outcome

Olefin cross metathesis on solid support under a variety of conditions is described. A comprehensive analysis considering diverse factors governing the reaction outcome gives a series of patterns for the application of this useful methodology in organic synthesis. If the intrasite reaction is not possible, homodimerization of the soluble olefin is crucial. When the homodimer is less reactive than its monomer, reaction outcome depends on the homodimerization rate, which, in turn, depends on the precatalyst used and the reaction conditions. If the site-site interaction is a feasible process, the cross metathesis product is obtained exclusively when the newly-formed double bond is resilient to further metathetic events. Taking into account these considerations, we have demonstrated that excellent results in terms of cross metathesis coupling can be obtained under the optimized conditions, and that microwave irradiation is also an interesting alternative for the development of a practical and energy-efficient cross metathesis on solid support.

Solid-supported cross metathesis and the role of the homodimerization of the non-immobilized olefin

(Chemical Equation Presented) We have prepared immobilized olefins as models for the cross metathesis using different olefin partners in the presence of second generation Grubbs and Hoveyda-Grubbs precatalysts. We have demonstrated that solid-phase cross metathesis is strongly dependent on the degree of homodimerization of the non-immobilized olefin and the reactivity of such a homodimer. As in the homogeneous phase, the Hoveyda-Grubbs precatalyst was better for immobilized α,β-unsaturated carbonyl compounds.

Direct reaction of dibromoacetic acid with aldehydes promoted by samarium diiodide: An easy, efficient, and rapid synthesis of (E)-α,β- unsaturated carboxylic acids with total stereoselectivity

A promoted SmI2 direct reaction of dibromoacetic acid with different aldehydes, followed by an elimination reaction also promoted by samarium diiodide, affords (E)-α,β-unsaturated carboxylic acids 2 with total stereoselectivity. A mechanism to explain this transformation is proposed.

On the mechanism of the selenolactonization reaction with selenenyl halides

The mechanism of selenocyclization reactions of β,γ-unsaturated acids and their derivatives has been studied. The reactions of (E)-4-phenyl-3-butenoic acid 10 and its silyl and alkyl esters with benzeneselenenyl chloride (PhSeCl) and bromide (PhSeBr) have been examined by VT-NMR and in situ IR spectroscopic methods. Whereas the reactions of the acid 10 in the presence of a base were irreproducible and complicated, reactions of the silyl esters were clean and spontaneously and quantitatively afforded a chloroselenylation adduct at -70 °C as a single (Markovnikov) isomer. This adduct underwent three processes as the temperature was raised: (1) reversal to the starting materials, (2) isomerization to the anti-Markovnikov product, and (3) cyclization to the selenolactone 12. All of these processes are believed to proceed via a seleniranium ion the intermediacy of which was established by independent synthesis and spectroscopic identification. The reversible formation of chloro selenide adducts was unambiguously established by crossover experiments. The reaction of 10 with PhSeBr was found to be rapid but thermodynamically unfavorable at room temperature.

KOH-promoted reaction of C,O,O-tris(trimethylsilyl) ketene acetal with aldehydes: Practical and easy access to (E)-α,β-ethylenic carboxylic acids

The use of a catalytic amount of KOH has been found to be very efficient in promoting reaction of silylketene acetal 1 with aldehydes 2 to afford the corresponding (E)-α,β-ethylenic carboxylic acids 3 under very mild conditions.

Meta, para and ortho double exo nucleophilic additions of trimethylsilylester enolates derived from saturated and unsaturated carboxylic acids to tricarbonylchromium complexes of aryl ethers: dearomatizing cyclization to lactones

Potassium enolates derived from saturated and unsaturated bis(trimethylsilyl) ketene acetals react with tricarbonylchromium complexes of anisole and diphenylether to give, in addition to α-arylcarboxylic acids, the mono addutcts, lactones, arising from a double exo nucleophilic addition. The latter were not observed in the case of benzenetricarbonylchromium. The intermediate dienol ethers could be isolated and fully characterized by X-ray crystallography. The influenece of the nature of the substituents on the ketene acetals, of the nature of the oxidant, and of the nature of the ester enolates on the course of the reaction has been established and will be discussed.