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Continued Progress towards Efficient Functionalization of Natural and Non‐natural Targets under Mild Conditions: Oxygenation by C−H Bond Activation with Dioxirane
Author(s) -
D'Accolti Lucia,
Annese Cosimo,
Fusco Caterina
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901687
Subject(s) - dioxirane , reactivity (psychology) , chemistry , steric effects , catalysis , molecule , organic chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
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.