34909-37-0

Usage

Molar mass

255.35 g/mol

Potential applications

pharmaceuticals, organic synthesis

Handle with caution

potential hazards if not handled properly

Upstream product

• 1866-39-3 4-methylcinnamic acid 
• 124-40-3 dimethyl amine 
• 127-19-5 N,N-dimethyl acetamide 
• 589-18-4 4-Methylbenzyl alcohol 
• 2680-03-7 N,N-Dimethylacrylamide 
• 5720-05-8 4-methylphenylboronic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 99-94-5 p-Toluic acid 
• 137-26-8 Thiram 
• 1866-39-3 trans-p-methylcinnamic acid 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 1866-39-3 4-methylcinnamic acid 

Relevant academic research and scientific papers

Palladium-Catalyzed Decarbonylative Heck Coupling of Aromatic Carboxylic Acids with Terminal Alkenes

A palladium-catalyzed decarbonylative alkenylation of aromatic carboxylic acids was developed. Under the reaction conditions, various benzoic acids including those bearing functional groups coupled to terminal alkenes, producing the corresponding internal alkenes in good to high yields. Cinnamic acids and bioactive benzoic acids such as 3-methylflavone-8-carboxylic acid, probenecid, adapalin, and febuxostat were also applicable to this reaction, demonstrating the potential synthetic value of this new reaction in organic synthesis.

Synthesis of Cinnamides via Amidation Reaction of Cinnamic Acids with Tetraalkylthiuram Disulfides Under Simple Condition

A facile and efficient methodology for the synthesis of cinnamides has been achieved under metal- and additive-free conditions. This method allows the efficient C–N cross-coupling of diverse cinnamic acids with tetraalkylthiuram disulfides through a simply mixing operation in 1,2-dichloroethane at 100 °C. The protocol provides a direct approach to cinnamides and is featured with readily available starting materials and broad substrate scope, which shows its practical synthetic value in organic synthesis.

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh2 species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPAr1Ar2) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords P-chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. 1H NMR studies show that the precoordination of HPPh2 to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(R,RP)-TANIAPHOS complex in the presence of excessive HPPh2, confirmed by 31P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh2 would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.

Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides

Oxidative cross-coupling reactions of benzyl alcohols with N,N-dialkylacetamides were developed only employing oxygen as the terminal oxidant, efficiently providing a new, novel protocol for the construction of multifunctionalized cinnamides with the synergistic effects of KOH, organic photocatalyst eosin Y, and visible light irradiation at room temperature. A broad substrate scope and mild reaction conditions are the prominent features of this transformation.

Ni-Catalyzed Α-Alkylation of Unactivated Amides and Esters with Alcohols by Hydrogen Auto-Transfer Strategy

A transition-metal-catalyzed borrowing hydrogen/hydrogen auto-transfer strategy allows the utilization of feedstock alcohols as an alkylating partner, which avoids the formation of stoichiometric salt waste and enables a direct and benign approach for the construction of C-N and C?C bonds. In this study, a nickel-catalyzed α-alkylation of unactivated amides and ester (tert-butyl acetate) is carried out by using primary alcohols under mild conditions. This C?C bond-forming reaction is catalyzed by a new, molecularly defined nickel(II) NNN-pincer complex (0.1–1 mol %) and proceeds through hydrogen auto-transfer, thereby releasing water as the sole byproduct. In addition, N-alkylation of cyclic amides under Ni-catalytic conditions is demonstrated.

Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C-C bond activation

Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.

Oxidative coupling of alkenes with amides using peroxides: Selective amide C(sp3)-H versus C(sp2)-H functionalization

A new oxidative coupling of unactivated terminal alkenes with amides using peroxides is described, in which mono- and difunctionalization of alkenes are selectively achieved. In this reaction with amides, the chemoselectivity toward the functionalization of the C(sp3)-H bonds adjacent to the nitrogen atom or the functionalization of the carbonyl C(sp2)-H bonds across alkenes relies on the reaction conditions. This journal is

Copper-catalyzed oxidative coupling of carboxylic acids with formamides for the synthesis of α,β-unsaturated amides

A novel and efficient protocol for the synthesis of α,β- unsaturated amides has been developed using catalytic amount of Cu(OAc) 2 and TBHP as an available oxidant. Oxidative coupling of various unsaturated carboxylic acids with N,N-disubstituted formamides was examined to furnish the desired products in good yields.

Copper-catalyzed synthesis of α,β-unsaturated acylamides via direct amidation from cinnamic acids and N-substituted formamides

A highly effective synthesis of α,β-unsaturated acylamides is reported for the first time via copper-catalyzed direct amidation between readily available cinnamic acids and N-substituted formamides. The protocol was easily accessible and practical.