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A Review on the Scope of TFDO-Mediated Oxidation in Organic Synthesis-Reactivity and Selectivity
Univ Karachi, HEJ Res Inst Chem, Int Ctr Chem & Biol Sci, Karachi 75270, Pakistan.
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan.
Univ Karachi, HEJ Res Inst Chem, Int Ctr Chem & Biol Sci, Karachi 75270, Pakistan.
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2018 (English)In: Current Organic Synthesis, ISSN 1570-1794, E-ISSN 1875-6271, Vol. 15, no 8, p. 1091-1108Article, review/survey (Refereed) Published
Abstract [en]

Dioxiranes are three-membered strained ring peroxides that are typical archetype examples of electrophilic entities. A dioxirane-based oxidant named 3-methyl(trifluoromethyl)dioxirane (TFDO) is a fluorinated analogue of the extremely valuable oxidant dimethyldioxirane (DMDO). Owing to the strained three-membered ring and presence of electron-withdrawing trifluoromethyl group, TFDO is several times more reactive than DMDO and acts as a significant chemical reagent. Moreover, TFDO exhibits high regio-, chemo- and stereo-selectivity even under unusual reaction conditions, i.e. at pH values close to neutrality and at sub-ambient temperatures. The TFDO transfers an oxygen atom to "unactivated" carbon-hydrogen bonds of alkanes as well as to the double bonds of alkenes and also helps in oxidation of compounds containing heteroatoms having a lone pair of electrons, such as sulfides and amines. TFDO-mediated oxidation is considered to be one of the main procedures in the 21st century for the synthesis of oxygen-containing organic molecules. This review throws light on the applications of TFDO in organic syntheses to provide an insight into the future research and gives a comprehensive summary of the selective functionalization of activated and non-activated organic compounds.

Place, publisher, year, edition, pages
2018. Vol. 15, no 8, p. 1091-1108
Keywords [en]
Dioxiranes, methyl(trifluoromethyl)dioxirane, TFDO, dimethyldioxirane, C-H activation, selectivity, reactivity, functionalization
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-373091DOI: 10.2174/1570179415666180831104324ISI: 000453372800004OAI: oai:DiVA.org:uu-373091DiVA, id: diva2:1277922
Available from: 2019-01-11 Created: 2019-01-11 Last updated: 2019-01-11Bibliographically approved

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El-Seedi, Hesham

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