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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Review Article

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 and Zulfiqar Ali Solangi

Volume 15, Issue 8, 2018

Page: [1091 - 1108] Pages: 18

DOI: 10.2174/1570179415666180831104324

Price: $65

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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