680980-39-6

Upstream product

• 79-21-0 peracetic acid 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 75-07-0 acetaldehyde 

Downstream Products

• 154715-81-8 2-(3,5-dimethylphenyl)-1,3-benzoxazole 
• 121957-03-7 3,5-dimethyl-1-iodosylbenzene 
• 1429318-42-2 di-(3,5-dimethylphenyl)iodoniumtriflate 

Relevant academic research and scientific papers

Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts

A novel approach to the preparation of imidazole-substituted cyclic iodonium salts has been developed via the oxidative cyclization of 1-phenyl-5-iodoimidazole using a cheap and available Oxone/H2SO4 oxidative system. The structure of the new polycyclic heteroarenes has been confirmed by single-crystal X-ray diffractometry, revealing the characteristic structure features for cyclic iodonium salts. The newly produced imidazole-flanked cyclic iodonium compounds were found to readily engage in a heterocyclization reaction with elemental sulfur, affording benzo[5,1-b]imidazothiazoles in good yields.

Spatial anion control on palladium for mild C-H arylation of arenes

C-H arylation of arenes without the use of directing groups is a challenge, even for simple molecules, such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C-H bond activation, thereby enabling nondirected C-H arylation of arenes at ambient temperature. The mild conditions enable late-stage structural diversification of biologically relevant small molecules, and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C-H bonds under mild conditions.

SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN

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

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

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.

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.

Direct arylation of benzoxazole C-H bonds with iodobenzene diacetates

A Pd (OAc)2-catalyzed direct arylation of benzoxazole C-H bonds has been achieved with iodobenzene diacetates as the arylation reagent in moderate to good yields. The procedure tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, and bromo groups.

Synthesis of 3-aryloxy-2-iodoemodines by oxidation of emodin with (diacetoxyiodo)arenes

Hypervalent iodine oxidation of emodin (1) with various (diacetoxyiodo)arenes 2a-f in potassium hydroxide/methanol leading to 3-aryloxy-1,8-dihydroxy-2-iodo-anthraquinones 4a-f is reported. Mechanistic studies showed reaction via iodonium ylides. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of functionalised unsymmetrical diaryliodonium salts

A generalised synthesis of unsymmetrical functionalised diaryliodonium salts has been developed through the direct reaction of bis(acetoxy)iodoarenes with arenes in a trifluoromethanesulfonic or trifluoroacetic acid medium.