130317-77-0

Upstream product

• 2680-03-7 N,N-Dimethylacrylamide 
• 529-28-2 4-iodoanisol 
• 135-02-4 ortho-anisaldehyde 
• 440357-42-6 N,N-dimethyl(triphenylsilyl)acetamide 
• 127-19-5 N,N-dimethyl acetamide 
• 90-02-8 salicylaldehyde 
• 616-38-6 carbonic acid dimethyl ester 
• 1011-54-7 2-methoxycinnamic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 612-16-8 (2-methoxyphenyl)methanol 

Relevant academic research and scientific papers

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.

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.

Cu(II)-Mediated keto C(sp3)-H bond α-acyloxylation of N, N-dialkylamides with aromatic carboxylic acids

The selective oxidative coupling of aromatic carboxylic acids with the C(sp3)-H bond adjacent to the keto group of alkylamides has been developed by employing a low cost copper source. This provides an efficient approach for synthesis of O-benzoylglycolamides. The protocol displayed good functional group tolerance. A broad range of benzoic acids directly coupled with alkylamides to afford a variety of O-benzoylglycolamides in moderate to good yields. In addition, a reasonable radical mechanism was proposed based on EPR experiments.

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.

Aldol condensation of amides using phosphazene-based catalysis

We have developed a new method for the direct aldol condensation of unactivated amides using 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6- hexachloride (TAPC)-based phosphorous/SO42- catalysis. The SO42- species in a reaction mixture enhances the reaction rate of the catalysis. In principle, no metal sources are required for the generation of the catalyst, and there is no requirement for the use of stoichiometric quantities of an acid or base. This catalyst system is operative under relatively acidic conditions. One major advantage of carrying out the reaction under acidic conditions is that both aldehydes and acetals are capable of undergoing carbon-carbon bond formation at the α-carbon of amide carbonyl groups through dehydration.

Condensation of aromatic aldehydes with VyV-dimethylacetamide in presence of dialkyl carbonates as dehydrating agents

Reactions of benzaldehydes with excess N,N- dimethylacetamide at 140 °C in the presence of diethyl carbonate as dehydrating agent and a base gave (E)-N,N- dimethylcinnamamides in good yields. If hydroxybenzal- dehydes are used as substrates the reaction is accompanied by alkylation. Springer-Verlag 2010.

Z-selective synthesis of α,β-unsaturated amides with triphenylsilylacetamides

With the purpose of developing a method of preparing Z-α,β-unsaturated amides, the Peterson reaction of the (triphenylsilyl)acetamide Ph3SiCH2COX (1, X = NBn2; 3, X = NMe2) with various aldehydes was examined. The reaction of aromatic aldehydes gave selectivities up to >97:3. It was found that the selectivity was a function of the electronic nature of the aromatic ring and higher Z selectivity was attained with electron-rich aldehydes. With aliphatic aldehydes selectivities up to 92:8 were achieved, and unlike with analogous phosphorus reagents, less sterically hindered aldehydes gave higher Z selectivity. Also, 3, which has a smaller amide group than 1, tended to give rise to higher selectivity. A comparison with the reaction of trimethylsilyl analogues revealed the significance of the phenyl substituents on the silyl group.

An interesting chloride ion effect in the Heck reaction

Addition of chloride ion is found to enhance the yields of cross-couplings between aryl iodides and selected olefin acceptors.