7697-57-6

Upstream product

• 7697-58-7 Ethyl 2-cyclohexylprop-2-enoate 
• 626-62-0 Cyclohexyl iodide 
• 931-48-6 2-cyclohexylacetylene 
• 124-38-9 carbon dioxide 
• 64-18-6 formic acid 
• 4354-67-0 2-cyclohexylmalonic acid 
• 108-85-0 1-bromocyclohexane 
• 931-50-0 cyclohexylmagnesium bromide 
• 13275-31-5 ethyl cyclohexyloxoacetate 
• 2163-44-2 diethyl 2-cyclohexylmalonate 
• 7697-61-2 2-cyclohexylacrylaldehyde 
• 3070-72-2 2-cyclohexylacrylic acid methyl ester 
• 50-00-0 formaldehyd 

Downstream Products

• 100860-76-2 2-cyclohexyl-acryloyl chloride ; chloride 
• 1279110-79-0 phenyl 2-cyclohexylprop-2-enoate 
• 6051-13-4 2-cyclohexylpropanoic acid 
• 1565870-35-0 3-cyclohexyl-4-nitrofuroxan 
• 2511-00-4 Ethyl 2-cyclohexylpropionate 
• 74255-29-1 C₁₁H₁₇NO₂ 
• 74255-34-8 3-cyclohexyl-1,3-dimethylazetidine-2,4-dione 
• 7697-58-7 Ethyl 2-cyclohexylprop-2-enoate 

Relevant academic research and scientific papers

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes with Carbon Dioxide

A Pd-catalyzed highly regioselective hydrocarboxylation of alkynes with carbon dioxide has been established. By the combination of Pd(PPh3)4 and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (binap), a variety of functionalized alkynes, including aryl alkynes, aliphatic alkynes, propargylamines, and propargyl ethers, could be leveraged to provide a wide array of α-acrylic acids in high yields with high regioselectivity under mild reaction conditions. Experimental and DFT mechanistic studies revealed that this reaction proceeded via the cyclopalladation process of alkynes and carbon dioxide in the presence of binap to generate a five-membered palladalactone intermediate and enabled the formation of Markovnikov adducts. Moreover, this strategy provided an effective method for the late-stage functionalization of alkyne-containing complicated molecules, including natural products and pharmaceuticals.

Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes

An efficient and convenient copper-mediated method has been developed to achieve direct cascade C-H/N-H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C-H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C-H activation via a Cu(iii) intermediate is likely to be involved in the reaction.

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water

A catalytic protocol that reliably predicts and controls the site-selective incorporation of CO2 to a wide range of unsaturated hydrocarbons utilizing water as formal hydride source is described. This platform unlocks an opportunity to catalytically repurpose three abundant, orthogonal feedstocks under mild conditions.

Nickel-catalyzed hydrocarboxylation of alkynes with formic acid

A protocol for nickel-catalyzed hydrocarboxylation of alkynes with formic acid was developed. The protocol allowed for highly efficient synthesis of acrylic acid with a TON of up to 7700.

Method for synthesizing alpha, beta-unsaturated acid by using formic acid and alkine

The invention relates to a method for synthesizing alpha, beta-unsaturated acid by using formic acid and alkine, in particular to a method for synthesizing alpha, beta-unsaturated acid by using formic acid and alkine under the effect of a nickel catalyst. The consumption of the catalyst is 0.01 to 2 mol percent of the quantity of a substrate substance; the consumption of estolide is 3 to 30 mol percent of the quantity of the substrate substance; the pressure of acetylene gas is 1 to 10 MPa; the reaction temperature is 25 to 100 DEG C; the reaction time is 5 to 12 hours. The method has the advantages that the existing alkine hydrocarboxylation defects are overcome; the use of toxic carbon monoxide gas does not needed; the reaction conditions of the whole process are mild; the efficiency is high; the selectivity is good; the method belongs to a method for preparing the alpha, beta-unsaturated acid with the advantages that the method conforms to green chemistry and has good application aspects; good industrial application prospects are realized.

Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters

The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described. The strong Br?nsted basicity of the iminophosphorane moiety of the catalyst provides the necessary activation of the alkyl thiol pro-nucleophile, while the two tert-leucine residues flanking a central thiourea hydrogen-bond donor facilitate high enantiofacial selectivity in the protonation of the transient enolate intermediate. The reaction is broad in scope with respect to the alkyl thiol, the ester moiety, and the α-substituent of the α,β-unsaturated ester, affords sulfa-Michael adducts in excellent yields (up to >99%) and enantioselectivities (up to 96% ee), and is amenable to decagram scale-up using catalyst loadings as low as 0.05 mol %.

Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates

Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.