54376-74-8

Upstream product

• 85-44-9 phthalic anhydride 
• 540-37-4 p-aminoiodobenzene 
• 524-38-9 N-hydroxyphthalimide 
• 933-88-0 ortho-toluoyl chloride 
• 83-33-0 inden-1-one 
• 136918-14-4 phthalimide 
• 591-50-4 iodobenzene 
• 66569-04-8 N-(4-iodophenyl)-2-methylbenzamide 
• 5122-99-6 4-iodophenylboronic acid 

Downstream Products

• 5383-82-4 4-phthalimidobenzoic acid 
• 909038-88-6 4-((E)-3,4,5-tripropoxystyryl)aniline 
• 1185761-53-8 C₃₃H₃₃N₃O₆ 
• 93-98-1 N-phenyl benzoyl amide 
• 52807-29-1 N-(4-iodophenyl)benzamide 
• 5383-83-5 4–(1,3-dioxoisoindolin-2-yl)benzoyl chloride 
• 127934-54-7 methyl 4-(1,3-dioxoisoindolin-2-yl)benzoate 

Relevant academic research and scientific papers

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.

Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition

A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.

Palladium-Catalyzed β-Arylation of Amide via Primary sp3C-H Activation

A β-arylation of primary sp3C-H bonds on simple amides such as pivalamides with aryl iodides/CF3CO2Ag has been established successfully at 120 °C in a Pd(OAc)2 (catalyst)/CF3CH2OH (solvent) system. Pivalamides including tBuCONH2, tBuCONHR, and tBuCONR2 undergo the arylations smoothly to afford β-aryl pivalamides in moderate to good yields. Various aryl iodides are available bearing either electron-donating or electron-withdrawing substituted groups in the coupling reactions.

Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides

A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.

Synthetic method for N-substituted imide

The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.

Phthalimide-N-sulfonic acid, an efficient catalyst for the synthesis of various isoindoline-1,3-dione derivatives

An environmentally friendly method is described for the synthesis of various isoindoline-1,3-dione derivatives from the reaction of phthalic anhydride with aromatic/aliphatic amines in ethanol at 80 °C by phthalimide-N-sulfonic acid as an efficient heterogeneous acid catalyst. Some advantages include the metal-free and environmentally friendly protocol, simple operation and reusable processes, easy recovery, short reaction times, and high yields.

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Thermolysis and radiofluorination of diaryliodonium salts derived from anilines

Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.

Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines

Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.