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

[ Vol. 15 , Issue. 8 ]

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 and Zulfiqar Ali Solangi   Pages 1091 - 1108 ( 18 )

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.

Affiliation:

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Division of Pharmacognosy, Department of Medicinal Chemistry, Uppsala University, Box 574, SE-75 123, Uppsala, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Department of Chemical Engineering, University of Hai'l, Hai'l, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Department of Chemistry, Allama Iqbal Open University, Islamabad 44000, Department of Chemistry, Shah Abdul Latif University, Khairpur



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