120866-17-3

Upstream product

• 352-34-1 4-fluoro-1-iodobenzene 
• 16308-15-9 (4-fluorophenyl)-λ³-iodanediyl diacetate 

Downstream Products

• 59696-13-8 (4-fluoro-phenyl)-phenyl-iodonium ; bromide 
• 26735-57-9 p-fluorophenyliodine difluoride 
• 56391-48-1 C₂₀H₁₂FIN₂O₁₀ 
• 56391-50-5 C₂₈H₃₀FIO₆ 
• 16669-00-4 1-fluoro-4-iodoxybenzene 
• 29848-54-2 4-(tetrafluoroiodo)fluorobenzene 
• 29848-52-0 4-fluorobenzene 

Relevant academic research and scientific papers

Oxidase catalysis via aerobically generated hypervalent iodine intermediates

The development of sustainable oxidation chemistry demands strategies to harness O'2 as a terminal oxidant. Oxidase catalysis, in which O'2 serves as a chemical oxidant without necessitating incorporation of oxygen into reaction products, would allow diverse substrate functionalization chemistry to be coupled to O'2 reduction. Direct O'2 utilization suffers from intrinsic challenges imposed by the triplet ground state of O'2 and the disparate electron inventories of four-electron O'2 reduction and two-electron substrate oxidation. Here, we generate hypervalent iodine reagents - a broadly useful class of selective two-electron oxidants - from O'2. This is achieved by intercepting reactive intermediates of aldehyde autoxidation to aerobically generate hypervalent iodine reagents for a broad array of substrate oxidation reactions. The use of aryl iodides as mediators of aerobic oxidation underpins an oxidase catalysis platform that couples substrate oxidation directly to O'2 reduction. We anticipate that aerobically generated hypervalent iodine reagents will expand the scope of aerobic oxidation chemistry in chemical synthesis.

Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?

An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.

SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN

Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.

Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors

Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.

Metal-Free O-Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes

The metal-free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly-polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings. (Figure presented.).