AI Article Synopsis
- The isolation of dioxirane in 1988 revolutionized the oxidation of various molecules, establishing it as a key tool in organic chemistry.
- Dioxiranes are recognized for their effectiveness in facilitating oxygen transfer, particularly in epoxidation and C-H bond reactions, while demonstrating high selectivity.
- This review highlights recent advancements in the use of isolated dioxiranes and their ketone precursors as organocatalysts for the selective oxyfunctionalization of non-activated C-H bonds in both natural and synthetic compounds.
Article Abstract
The successful isolation and characterization of a dioxirane species in 1988 opened up one of the most attractive methods for the efficient oxidation of simple and/or structurally complex molecules. Dioxirane today rank among the most powerful tools in organic chemistry, with numerous applications in commercially important processes. They were quickly recognized as efficient oxygen transfer agents, especially for epoxidations and for a wide range of O-insertion reactions into C-H bonds. Dioxirane possess catalytic activity and appear as highly (chemo-, regio-, and stereo-) selective oxidants, despite their reactivity under mild and strictly neutral conditions being controlled by a combination of steric and electronic factors. In this review, we discuss some of the most recent and significant developments in the selective homogeneous and heterogeneous oxyfunctionalization of non-activated C-H bonds in hydrocarbons of natural and non-natural targets by using isolated dioxirane or, more generally, by using the ketones (i.e., the dioxirane precursors) as organocatalysts.
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| http://dx.doi.org/10.1002/chem.201901687 | DOI Listing |
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