Title:A Review on the Scope of TFDO-Mediated Oxidation in Organic Synthesis-- Reactivity and Selectivity
Volume: 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
Affiliation:
- Department of Chemistry, Quaid-i-Azam University, Islamabad 45320,Pakistan
- Department of Chemistry, Quaid-i-Azam University, Islamabad 45320,Pakistan
- Department of Chemistry, Quaid-i-Azam University, Islamabad 45320,Pakistan
Keywords:
Dioxiranes, methyl(trifluoromethyl)dioxirane, TFDO, dimethyldioxirane, C-H activation, selectivity; reactivity, functionalization.
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.
