120866-17-3Relevant articles and documents
Oxidase catalysis via aerobically generated hypervalent iodine intermediates
Maity, Asim,Hyun, Sung-Min,Powers, David C.
, p. 200 - 204 (2018)
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 HYPERVALENT IODINE REAGENTS WITH DIOXYGEN
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, (2019/01/15)
Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.
Metal-Free O-Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes
Dohi, Toshifumi,Koseki, Daichi,Sumida, Kohei,Okada, Kana,Mizuno, Serina,Kato, Asami,Morimoto, Koji,Kita, Yasuyuki
, p. 3503 - 3508 (2017/09/13)
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.).