TY - JOUR
T1 - Dioxiranes
T2 - a half-century journey
AU - El-Assaad, Tarek H.
AU - Zhu, Jayden
AU - Sebastian, Anjitha
AU - McGrath, Dominic V.
AU - Neogi, Ishita
AU - Parida, Keshaba N.
N1 - Funding Information:
KNP acknowledges the CSIR for a Senior Research Associateship. AS acknowledges DST Inspire for as JRF fellowship. IN acknowledges CSIR-NIIST for facility.
Publisher Copyright:
© 2022 The Royal Society of Chemistry.
PY - 2022/8/15
Y1 - 2022/8/15
N2 - Dioxiranes are multi-tasking reagents with mild and selective oxygen transfer attributes. These oxidants are accessed from the reaction of ketones with an oxidant and are employed stoichiometrically or catalytically (in situ) for numerous transformations such as oxidations, epoxidations, C-H hydroxylation, etc. The oxidations involve a broad spectrum of substrates such as alcohols, amines, phenols, silanes, phosphines, etc. Similarly, the epoxidation of olefins, alkynes, allenes and arenes is achieved efficiently, where alkene epoxidation can be regioselective, chemoselective, stereoselective, and stereospecific. Furthermore, C-H hydroxylation using dioxiranes proceeds in both an inter- and intramolecular fashion producing a variety of potent molecules that are difficult to access using other means. Dioxiranes are used for the synthesis of various natural products, drugs, and biomolecules. This review covers all the aforementioned aspects of dioxirane chemistry along with the historical development, characteristics, and reaction mechanisms of dioxirane-mediated transformations established over the last five decades.
AB - Dioxiranes are multi-tasking reagents with mild and selective oxygen transfer attributes. These oxidants are accessed from the reaction of ketones with an oxidant and are employed stoichiometrically or catalytically (in situ) for numerous transformations such as oxidations, epoxidations, C-H hydroxylation, etc. The oxidations involve a broad spectrum of substrates such as alcohols, amines, phenols, silanes, phosphines, etc. Similarly, the epoxidation of olefins, alkynes, allenes and arenes is achieved efficiently, where alkene epoxidation can be regioselective, chemoselective, stereoselective, and stereospecific. Furthermore, C-H hydroxylation using dioxiranes proceeds in both an inter- and intramolecular fashion producing a variety of potent molecules that are difficult to access using other means. Dioxiranes are used for the synthesis of various natural products, drugs, and biomolecules. This review covers all the aforementioned aspects of dioxirane chemistry along with the historical development, characteristics, and reaction mechanisms of dioxirane-mediated transformations established over the last five decades.
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U2 - 10.1039/d2qo01005d
DO - 10.1039/d2qo01005d
M3 - Review article
AN - SCOPUS:85138659258
SN - 2052-4110
VL - 9
SP - 5675
EP - 5725
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
IS - 20
ER -