19169-99-4

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 64-19-7 acetic acid 
• 2754-27-0 trimethylsilyl acetate 
• 64846-47-5 4-nitrobenzene 

Downstream Products

• 62443-84-9 C₇H₄IN₃O₆ 
• 161564-36-9 1--4-nitrobenzene 
• 69003-40-3 1-iodosyl-4-nitrobenzene 
• 1039396-25-2 (E)-1-methyl-3-((4-nitrophenyl)(phenyl)methylene)indolin-2-one 
• 1220515-91-2 3-[(2,4-difluorophenyl)(4-nitrophenyl)amino]-2-iodocyclohex-2-enone 
• 1220516-06-2 3-[cyclohexyl(4-nitrophenyl)amino]-2-iodocyclohex-2-enone 
• 1220516-04-0 2-iodo-3-[(4-nitrophenyl)(phenethyl)amino]cyclohex-2-enone 
• 1220515-86-5 2-iodo-3-[(4-methoxyphenyl)(4-nitrophenyl)amino]cyclohex-2-enone 
• 1220515-95-6 3-(benzyl(4-nitrophenyl)amino)-2-iodocyclohex-2-enone 
• 1396650-10-4 2-iodo-5,5-dimethyl-3-((4-nitrophenyl)(phenyl)amino)cyclohex-2-enone 
• 1220515-77-4 2-iodo-3-[(4-nitrophenyl)(phenyl)amino]cyclohex-2-enone 
• 1396650-03-5 3-(bis(4-nitrophenyl)amino)-2-iodocyclohex-2-enone 

Relevant academic research and scientific papers

Remote Substituents as Potential Control Elements for the Solid-State Structures of Hypervalent Iodine(III) Compounds

Hypervalent iodine (HVI) compounds are very important selective oxidants often employed in organic syntheses. Most HVI compounds are strongly associated in the solid state involving interactions between the electropositive iodine centers and nearby electr

Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

A practical method for the preparation of (diacetoxyiodo)arene ArI(OAc)2 is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H2O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.

The Coming of Age in Iodane-Guided ortho-C?H Propargylation: From Insight to Synthetic Potential

As early as 1991 Ochiai et al. reported that an acid-activated form of phenyliodine diacetate, PhI(OAc)2, undergoes a reaction with propargyl-silanes, germanes and stannanes to give the ortho-propargyl iodobenzene. This formal C?H alkylation wa

N -Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts to Generate α,β-Unsaturated Ketones

An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.

An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [18F]Fluoroarenes from Cyclotron-Produced [18F]Fluoride Ion

Treatment of (diacetoxyiodo)arenes (1a-1u) with cyclotron-produced [18F]fluoride ion rapidly affords no-carrier-added [18F]fluoroarenes (2a-2u) in useful yields and constitutes a new method for converting substituted iodoarenes into substituted [18F]fluoroarenes in just two steps.

NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles

The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3-iodanes are produced by treating the NH-imidazole with ArI(OAc)2, and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.

A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts

Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal reagents, and provides a direct route to stable precursors to PET imaging agents.

An alternative to the Sandmeyer approach to aryl iodides

Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

Simple and practical method for preparation of [(diacetoxy)iodo]arenes with iodoarenes and m-chloroperoxybenzoic acid

Various [(diacetoxy)iodo]arenes bearing 4-methylphenyl, phenyl, 4-nitrophenyl, 3-nitrophenyl, 4-cyanophenyl, 4-bromophenyl, 4- methoxycarbonyphenyl, 3,5-bis(trifluoromethyl)phenyl, and 4-(N,N,N- trimethylammonium)methylphenyl groups were efficiently prepared by the treatment of iodoarenes with m-chloroperoxybenzoic acid in acetic acid. The great advantage of the present method is the easy preparation and isolation of [(diacetoxy)-iodo]arenes bearing electron-withdrawing groups, such as 4-nitro, 4-cyano, 4-methoxycarbonyl, and 3,5-bis(trifluoromethyl) groups, on the aromatic ring.

NMR study on the structure and stability of 4-substituted aromatic iodosyl compounds

Two 4-substituted aromatic iodosyl compounds were investigated with regard to their solubility, stability and chromatographic behaviour. 1-Iodosyl-4-methoxy- and 1-iodosyl-4-nitro-benzene are soluble in methanol and provide acceptable 1H and s