A Review on the Scope of TFDO-Mediated Oxidation in Organic Synthesis-- Reactivity and Selectivity

Author(s): Shereena Shahid , Muhammad Faisal* , Aamer Saeed* , Sarfaraz Ali Ghumro , Hesham R. El-Seedi , Samina Rasheed , Nadir Abbas , Fayaz Ali Larik* , Pervaiz Ali Channar , Tanzeela Abdul Fattah , Zaman Ashraf , Zulfiqar Ali Solangi .

Journal Name: Current Organic Synthesis

Volume 15 , Issue 8 , 2018

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Graphical Abstract:


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 threemembered 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 subambient 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.

Keywords: Dioxiranes, methyl(trifluoromethyl)dioxirane, TFDO, dimethyldioxirane, C-H activation, selectivity; reactivity, functionalization.

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Article Details

Year: 2018
Page: [1091 - 1108]
Pages: 18
DOI: 10.2174/1570179415666180831104324
Price: $58

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