58265-36-4

Upstream product

• 5682-41-7 2,3-diphenyl-2-methylpropan-3-one oxime 
• 89372-28-1 1-(2-methyl-2-phenylpropanoyl)-1H-imidazole 
• 62-53-3 aniline 
• 826-55-1 2-methyl-2-phenylpropionic acid 
• 2901-13-5 ethyl 2-methyl-2-phenylpropionate 
• 98-95-3 nitrobenzene 
• 36293-05-7 2-methyl-2-phenylpropanoyl chloride 
• 2173-69-5 2-methyl-2-phenyl-propan-1-ol 
• 1678-25-7 N-phenylbenzenesulfonamide 
• 52412-43-8 5,5-dimethyl-3,4-diphenyl-4,5-dihydro-3H-[1,2,3]triazol-4-ol 
• 98-86-2 acetophenone 
• 201230-82-2 carbon monoxide 
• 98-83-9 isopropenylbenzene 
• 142-04-1 aniline hydrochloride 

Relevant academic research and scientific papers

Functionalization of α-C(sp3)?H Bonds in Amides Using Radical Translocating Arylating Groups

α-C?H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3)?H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes

Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations

Challenging couplings of hindered carboxylic acids with non-nucleophilic amines to form amide bonds can be accomplished in high yields, and in many cases, with complete retention of the adjacent stereogenic centers using the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI). This method allows for in situ generation of highly reactive acyl imidazolium ions, which have been demonstrated to be intermediates in the reaction. The reagent delivers high reactivity similar to acid chlorides with the ease of use of modern uronium reagents.

Rhodium-Catalyzed oxidative amidation of sterically hindered aldehydes and alcohols

A rhodium-catalyzed oxidative amidation reaction has been developed with sterically hindered aldehydes and alcohols for the synthesis of amides containing a quaternary carbon at the α position. A variety of amine nucleophiles, both aliphatic and aromatic, are employed and afford the corresponding amides in good to excellent yields. Finally, mechanistic studies are performed to gain insight into both catalytic cycles.

Visible Light-Induced Radical Rearrangement to Construct C-C Bonds via an Intramolecular Aryl Migration/Desulfonylation Process

A highly efficient intramolecular selective aryl migration/desulfonylation of 2-bromo-N-aryl-N-(arenesulfonyl)amide via visible light-induced photoredox catalysis has been accomplished. This approach allows for the construction of a variety of multisubstituted N,2-diarylacetamide under mild reaction conditions.

DBU catalysis of N,N'-carbonyldiimidazole-mediated amidations

(Figure presented) 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) has been found to catalyze the amidatlon of acyl imidazoles. The rate acceleration is especially evident with traditionally unreactlve, electron-deficient anilines. DBU is readily available and o

A comparison of catalysts to promote imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst

Five catalysts were compared with respect to their safety and catalytic effectiveness for promoting imidazolide couplings. Reaction rate enhancement, shock sensitivity, and differential scanning calorimetry (DSC) data were considered in this analysis. 6-Chloro-1-hydroxybenzotriazole, which has been described in the literature as a safe catalyst, was found to be shock sensitive. 2-Hydroxy-5-nitropyridine is a new catalyst for this type of reaction and was found to be safe, effective, readily available, and similar in price to that of the 1-hydroxybenzotriazole, a common catalyst for promoting acylation reactions.