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• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 107-92-6 butyric acid 
• 591-50-4 iodobenzene 
• 123-72-8 butyraldehyde 

Relevant academic research and scientific papers

A Catalyst-Free Minisci-Type Reaction: the C–H Alkylation of Quinoxalinones with Sodium Alkylsulfinates and Phenyliodine(III) Dicarboxylates

A direct C–H alkylation of quinoxalinones at the C-3 position with sodium alkylsulfinates and phenyliodine(III) dicarboxylates has been developed under catalyst-free conditions. A series of 3-alkylquinoxalinones were afforded in moderate to excellent yields in this protocol, which offers a practical and efficient access to biologically interesting 3-alkylquinoxalin-2(1H)-one derivatives.

Ligand exchange of aryl iodine dicarboxylates to form reagents with differing solubilities

Hypervalent iodine (HVI) reagents are employed in organic synthesis as versatile, proficient, and environmentally friendly reagents. Despite the utility of such reagents, the application of HVI reagents, especially phenyliodonium diacetate (PIDA), has been limited due to its poor solubility in a myriad of solvents. The aggregated and polymeric structures of many HVI reagents account for their poor solubility, thus limiting the reactivity and use of HVI reagents in reactions in non-polar solvents. The research presented herein outlines ligand exchange reactions of universal carboxylic acids promoted by phenyliodonium diacetate (PIDA) reagents, in which the acetate moiety of PIDA is modified, ultimately enhancing the solubility and reactivity of HVI reagents.

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.

Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation

Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.

Understanding the differential performance of Rh2(esp) 2 as a catalyst for C-H amination

(Chemical Equation Presented) Catalytic amination of saturated C-H bondsis performed efficiently with the use of Rh2(esp)2. Efforts to identify pathways for catalyst degradation and/or arrest have revealed a singleelectron oxidation event that gives rise to a red-colored, mixed-valence dimer, [Rh2(esp)2]+. This species is fortuitously reduced by carboxylic acid, a byproductgenerated in the reaction cycle with each turnover of the diacyloxyiodi ne oxidant. These findings have led to the conclusion that the high performance of Rh2(esp)2 is due in part to the superior kinetic stability of its one-electron oxidized form relative to other dimeric Rh complexes.