66166-42-5

Upstream product

• 100-02-7 4-nitro-phenol 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 177363-10-9 1-fluoro-2-iodo-4-nitrobenzene 
• 89487-91-2 2-iodo-4-nitrophenol 
• 72212-81-8 2-hydroxy-5-nitrodiphenyliodonium ylide 
• 64-19-7 acetic acid 
• 75-15-0 carbon disulfide 
• 66166-39-0 (2-hydroxy-5-nitro-phenyl)-phenyl-iodonium ; acetate 
• 5410-98-0 5-nitro-2-phenoxy-aniline 

Downstream Products

• 20927-95-1 2-nitrodibenzofuran 
• 833-77-2 (2,4-diiodo-phenyl)-phenyl ether 
• 860735-00-8 3-iodo-4-phenoxy-aniline 

Relevant academic research and scientific papers

Metal-Free Synthesis of Etherified 3-(1H-1,2,3-Triazol-1-yl)phenyl Iodides through O–H Arylation/C–H Iodination with Diacetoxyiodobenzenes

A concise and efficient method for the synthesis of etherified 3-(1H-1,2,3-triazol-1-yl)phenyl iodides from 1,4-disubstituted 1,2,3-triazoles under metal-free conditions has been developed. In the presence of ArI(OAc)2, a range of 1,2,3-triazole substrates that contain a hydroxy group underwent a direct O–H arylation and C–H iodination to afford functionalized 1,2,3-triazoles in good to excellent yields.

Diarylation of N- and O-nucleophiles through a metal-free cascade reaction

The arylation of heteroatom nucleophiles is a central strategy to reach diarylated compounds that are key building blocks in agrochemicals, materials, and pharmaceuticals. Nucleophilic aromatic substitution is a classical tool for such arylations, and recent developments in hypervalent iodine-mediated arylations allow a wider scope of products. Herein, we combine the benefits of these strategies to enable an efficient and transition-metal-free difunctionalization of N- and O-nucleophiles with two structurally different aryl groups and to provide di- and triarylamines and diaryl ethers in one single step (>100 examples). The core of this strategy is the unique reactivity discovered with specifically designed fluorinated diaryliodonium salts, which unveils novel reaction pathways in hypervalent iodine chemistry. The methodology is suitable for diarylation of aliphatic amines, anilines, ammonia, and even water. It tolerates a wide variety of functional and protecting groups, with the retained iodine substituent easily accessible for derivatization of the products.

Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed dehydrogenative C-H activation/annulation

In this report, we have described a FeCl3-catalyzed process involving intramolecular annulation of o-phenoxy diarylacetylenes via hydroarylation to afford a series of biologically potent fused seven-membered (6-7-6) ring compounds under mild reaction conditions. This reaction was believed to proceed through Friedel-Crafts type sequential carbometallation followed by protonation to produce phenyldibenz[b,f]oxepines. This method was also extended to synthesize seven-membered rings that are fused with coumarins.

One-pot syntheses of 2,6-diiododiaryl ethers from para-EWG-substituted phenols by diacetoxyiodobenzene

2,6-Diiododiaryl ethers are not only useful blocks to construct substituted diaryl ethers but are also characteristic drug precursors. In this research, a one-pot tandem oxidation of phenols substituted with electron-withdrawing group at the para position by excess diacetoxyiodobenzene is proven as a novel and efficient method for preparing 2,6-diiododiaryl ethers. Using this method, three new 2,6-diiododiaryl ethers, namely, methyl 3,5-diiodo-2-methoxy-4-phenoxybenzoate (2), methyl 3,5-diiodo-4-phenoxybenzoate (6), and 1-(2,6-diiodo-4-nitrophenoxy)benzene (7) were readily obtained from the corresponding phenols, and the yields were good.

One-Pot Assembly of Fused Heterocycles via Oxidative Palladium-Catalyzed Cyclization of Arylols and Iodoarenes

A one-pot, two-step cyclization reaction of iodoarenes with diversified arylols, including 4-hydroxyquinoline, quinolinone, 4-hydroxypyridine and phenol, has been developed. By using this palladium-catalyzed formal tandem O-arylation, dehydrogenative cross-coupling reaction, a variety of biologically significant fused benzo[4,5]furo heterocycles and dibenzofurans were quickly assembled in high yields with excellent regioselectivity. Notably, the efficient one-pot reaction led to the heterocycles via sequential oxidation, iodination, isomerization and cyclization steps without purification of any reaction intermediates.

Synthesis of Dibenzofurans via C-H Activation of o-Iodo Diaryl Ethers

An efficient method for the synthesis of dibenzofuran from o-iododiaryl ether using reusable Pd/C under ligand-free conditions has been developed. Synthesis of o-iododiaryl ether was achieved in one pot through sequential iodination and O-arylation of phenol under mild reaction conditions.

1,3-Oxathiole-2-thiones from the Reaction of Carbon Disulfide with Zwitterionic Iodonium Compounds

We have synthesized 1,3-oxathiole-2-thiones from the reaction of zwitterionic iodonium compounds with carbon disulfide.The reaction is shown to be photochemical and possible pathways are discussed.