19357-21-2

Upstream product

• 88-67-5 2-Iodobenzoic acid 
• 201230-82-2 carbon monoxide 
• 615-36-1 2-bromoaniline 
• 136918-14-4 phthalimide 
• 108-86-1 bromobenzene 
• 3481-09-2 N-chlorophthalimide 
• 85-44-9 phthalic anhydride 
• 615-42-9 1,2-Diiodobenzene 
• 610-97-9 o-iodo-methyl-benzoic acid 

Relevant academic research and scientific papers

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.

The aminocarbonylation of 1,2-diiodoarenes with primary and secondary amines catalyzed by palladium complexes with imidazole ligands

The efficient carbonylative cyclization of 1,2-diiodobenzene with different primary and secondary amines was performed using a palladium complex with an imidazole ligand, PdCl2(BIM)2, as a catalyst. In reactions performed at 1 atm of CO with primary amines, phthalimides were obtained as the only products with yields of up to 100% in 4 h. An even shorter time, 1 h, was sufficient to obtain the same products employing methyl-2-iodobenzoate as a substrate instead of 1,2-diiodobenzene. In an analogous reaction with secondary amines, 1,2-diiodobenzene was converted to three products, formed in amounts dependent on the reaction conditions. The presence of Pd NPs and soluble palladium intermediates indicated their participation in the catalytic reaction.

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.

Sterically controlled, palladium-catalyzed intermolecular amination of arenes

We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.

Carbonylative cyclization of o-halobenzoic acids for synthesis of N-substituted phthalimides using polymer-supported palladium-N-heterocyclic carbene as an efficient, heterogeneous, and reusable catalyst

The carbonylative cyclization of o-iodobenzoic acid with a variety of primary amines and carbon monoxide (1 bar) using a polymer-supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as the catalyst gives N-substituted 1H-isoindole-1,3(2H)-diones (phthalimides) in good to excellent yields with a short reaction time. The catalyst is efficient, heterogeneous, and phosphine-free, it exhibited remarkable activity and it is also recyclable (4 consecutive cycles). The use of methyl o-iodobenzoate as the substrate under these conditions also gave N-substituted 1H-isoindole-1,3(2H)-diones, but with lower yields. Cyclization of o-iodobenzyl alcohol with carbon monoxide under these conditions gave isobenzofuran-1(3H)-one (phthalide). Georg Thieme Verlag Stuttgart · New York.