109548-76-7

Upstream product

• 644-36-0 o-methylphenylacetic acid 
• 409359-85-9 2-(2-methylphenyl)propenoic acid ethyl ester 
• 64-18-6 formic acid 
• 766-47-2 1-ethynyl-2-methylbenzene 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 127560-52-5 methyl 2-(2-methylphenyl)acrylate 
• 40851-62-5 methyl o-tolylacetate 
• 95-46-5 2-methylphenyl bromide 
• 66644-67-5 ethyl 2-methylbenzoylformate 
• 67541-85-9 4-methyl-N'-(1-(2-methylphenyl)ethylidene)benzenesulfonohydrazide 
• 109548-75-6 2-(hydroxymethyl)phenylacetic acid 

Downstream Products

• 109548-79-0 6,7-Dimethoxy-1-(1-o-tolyl-ethyl)-3,4-dihydro-isoquinoline 
• 109548-81-4 8,9-Dimethoxy-1-o-tolyl-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline 
• 109548-80-3 3-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-yl)-3-o-tolyl-propan-1-ol 
• 109548-82-5 4-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-yl)-4-o-tolyl-butan-2-ol 
• 109548-83-6 4-(6,7-Dimethoxy-3,4-dihydro-isoquinolin-1-yl)-2-methyl-4-o-tolyl-butan-2-ol 
• 109548-78-9 6,7-Dimethoxy-1-(1-o-tolyl-vinyl)-3,4-dihydro-isoquinoline; hydrochloride 
• 144789-13-9 (S)-2-(2-methylphenyl)propanoic acid 
• 929030-18-2 (S)-1,3-dimethyl-3-o-tolylindolin-2-one 
• 143392-20-5 3-(2-methylphenyl)-2,5-dihydrofuran-2-one 

Relevant academic research and scientific papers

Cs2CO3-promoted carboxylation of N-tosylhydrazones with carbon dioxide toward α-arylacrylic acids

A Cs2CO3-promoted carboxylation of N-tosylhydrazones and CO2 has been developed. The reaction proceeded efficiently at 80 C under atmospheric CO2, gave the corresponding α-arylacrylic acids in moderate to good yields. This method was featured with (1) the employment of Cs2CO3 rather than nBuLi as the base; (2) a reaction temperature of 80 C rather than -78 C.

Palladium-Catalyzed Hydrocarboxylation of Alkynes with Formic Acid

A palladium-catalyzed hydrocarboxylation of alkynes with formic acid has been developed. The method provides acrylic acid and derivatives in good yields with high regioselectivity without the need to handle toxic CO gas. Nontoxic: Acrylic acids are an important chemical feedstock. The title reaction provides acrylic acid and derivatives in good yields with high regioselectivities without the need to handle toxic CO gas.

Rh-Catalyzed Coupling of Acrylic/Benzoic Acids with α-Diazocarbonyl Compounds: An Alternative Route for α-Pyrones and Isocoumarins

A coupling of acrylic acids/benzoic acids with α-diazocarbonyl compounds has been realized by a combined catalytic system of rhodium catalyst and Zn(OAc)2 additive. The presence of Zn(OAc)2 obviously accelerates the C(sp2)

Method for preparing alpha, beta-unsaturated carboxylic acid compound

The invention discloses a method for preparing an alpha, beta-unsaturated carboxylic acid compound, which comprises the following steps: 1) in an atmosphere containing carbon dioxide, heating and reacting a mixture containing hydrosilane and a copper catalyst to obtain a system I; and 2) adding a raw material containing alkyne and a nickel catalyst into the system I in the step 1), and heating to react. The method has the advantages of simple, easily available, cheap and stable raw materials, common, easily available and stable catalyst, mild reaction conditions, simple post-treatment, high yield and the like.

Water-initiated hydrocarboxylation of terminal alkynes with CO2and hydrosilane

This work discloses a Cu(ii)-Ni(ii) catalyzed tandem hydrocarboxylation of alkynes with polysilylformate formed from CO2and polymethylhydrosiloxane that affords α,β-unsaturated carboxylic acids with up to 93% yield. Mechanistic studies indicate that polysilylformate functions as a source of CO and polysilanol. Besides, a catalytic amount of water is found to be critical to the reaction, which hydrolyzes polysilylformate to formic acid that induces the formation of Ni-H active species, thereby initiating the catalytic cycle.

Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides

An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

Cobalt-Catalyzed Vinylic C-H Addition to Formaldehyde: Synthesis of Butenolides from Acrylic Acids and HCHO

A carboxyl-assisted C-H functionalization of acrylic acids with formaldehyde to give butenolides is described. It is the first time that the addition of an inert vinylic C-H bond to formaldehyde has been achieved via cobalt-catalyzed C-H activation. The unique reactivity of the cobalt species was observed when compared with related Rh or Ir catalysts. γ-Hydroxymethylated butenolides were produced by the treatment of Na2CO3 after the catalytic reaction in one pot.

3,3′-Disubstituted Oxindoles Formation via Copper-Catalyzed Arylboration and Arylsilylation of Alkenes

Arylboration and arylsilylation reactions of N-(2-iodoaryl)acrylamides with bis(pinacolato)-diboron (B2pin2) or PhMe2Si-Bpin are developed by using simple CuOAc as the sole catalyst. A range of boron-or silane-bearing 3,3′-disubstituted oxindoles are obtained in moderate to excellent yields. The reaction is proposed to proceed via a domino sequence involving intermolecular olefin borylcupration or silylcupration followed by intramolecular coupling of an alkyl-Cu intermediate with aryl iodide.

Co-catalysis over a tri-functional ligand modified Pd-catalyst for hydroxycarbonylation of terminal alkynes towards α,β-unsaturated carboxylic acids

An amphiphilic tri-functional ligand (L1) containing a Lewis acidic phosphonium cation, a phosphino-fragment and a hydrophilic sulfonate anion (-SO3-) enabled Pd(OAc)2 to efficiently co-catalyze the hydroxycarbonylation of terminal alkynes towards α,β-unsaturated carboxylic acids. These incorporated functional groups synergistically promoted the reaction, which proved more effective than the ligands lacking -SO3- and/or phosphonium and the mechanical mixtures of the individual functional groups independently. The molecular structure of Pd-L1 indicated that -SO3- in L1 served as a secondary O-donor ligand with reversible coordinating ability, cooperating with the phosphino-fragment to stabilize the Pd-catalyst. The in situ FT-IR analysis verified that the formation and stability of Pd-H active species in charge of hydroxycarbonylation were dramatically facilitated by the presence of L1. It was believed that, over the L1-based Pd-catalyst, H2O was cooperatively activated by the Lewis acidic phosphonium via "acid-base pair" interaction (H2O → P(v)+) and by the hydrophilic SO3-via hydrogen bonding (SO3-?H2O), giving rise to the formation of dimeric and mono-nuclear Pd-H species driven by reversible SO3--coordination. In addition, the L1-based Pd-catalyst could be immobilized in the ionic liquid [Bmim]NTf2 for six-run recycling uses without obvious activity loss and detectable metal leaching.