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Upstream product

• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 577-19-5 2-nitrophenyl bromide 
• 615-36-1 2-bromoaniline 
• 34713-70-7 2-Phenylpropanal 
• 3302-39-4 1-azido-2-bromobenzene 
• 25145-43-1 2-phenylpropionyl chloride 
• 6832-87-7 2-bromo-N-methylaniline 
• 492-37-5 hydratropic acid 
• 103-82-2 phenylacetic acid 

Downstream Products

• 1002357-07-4 N-benzyl-N-(2-bromophenyl)-2-phenylpropanamide 
• 1226555-99-2 C₁₅H₁₄BrNO 
• 1226556-01-9 C₁₅H₁₄BrNO 
• 349081-36-3 (+/-)-N-(2-bromophenyl)-N-methyl-2-phenylpropamide 

Relevant academic research and scientific papers

Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene

An efficient route for the palladium-catalyzed reductive aminocarbonylation of olefins with nitroarenes was developed using carbon monoxide (CO) as both reductant and carbonyl source, which enables facile access to amides with excellent regioselectivity a

Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes

Aryl amides have been used as important compounds in pharmaceuticals, materials and in molecular catalysis. The methods reported to prepare aryl amides generally require very specific reagents, and the most popular carboxyl-amine coupling reactions demand stoichiometric activators. Herein, we report that aryl azides react with aldehydes under base-catalyzed conditions to yield aryl amides efficiently. Mechanistic investigations support the formation of triazoline intermediates via azide-enolate cycloaddition, which subsequently undergo rearrangement to give amides by either thermal decomposition (20-140 °C) or aqueous acid work-up at room temperature. The strategy does not require nucleophilic anilines and is especially efficient for highly electron-deficient aryl amides, including perfluoroaryl amides, which are otherwise challenging to synthesize.

N, N -diethylurea-catalyzed amidation between electron-deficient aryl azides and phenylacetaldehydes

Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.

Synthesis of chiral N-heterocyclic carbene ligands with rigid backbones and application to the palladium-catalyzed enantioselective intramolecular α-arylation of amides

Chiral N-heterocyclic carbene (NHC) ligands having a 2,2′- bisquinoline-based C2 symmetric skeleton were developed. The ligands exhibited good enantioselectivity in palladium-catalyzed intramolecular α-arylation of amides to give 3,3-disubsituted oxindoles.

Bulky chiral carbene ligands and their application in the palladium- catalyzed asymmetric intramolecular α-arylation of amides

(Chemical Equation Presented) Bring on the big cats: New, C 2-symmetric bulky N-heterocyclic carbene ligands bring major improvements in the palladium-catalyzed asymmetric intramolecular α-arylation of amides to give oxindoles (see picture, dba=trans,trans- dibenzylideneacetone), which are formed in high yield and excellent enantiomeric purity.