Direct Oxidation of Csp3−H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

A fast, scalable, and safer Csp3−H oxidation of activated and un‐activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp3−H bonds. The proces...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-01, Vol.25 (5), p.1203-1207
Main Authors: Lesieur, Mathieu, Battilocchio, Claudio, Labes, Ricardo, Jacq, Jérôme, Genicot, Christophe, Ley, Steven V., Pasau, Patrick
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Continuous flow
Dioxirane
flow
Functional groups
hydroxylation
Oxidation
Oxone
Scale (corrosion)
TFDO
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Summary:A fast, scalable, and safer Csp3−H oxidation of activated and un‐activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp3−H bonds. The process exhibits a broad scope and good functional group compatibility (28 examples, 8–99 %). The scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane. Faster, safer, scalable: A continuous flow concept allowed the direct Csp3−H oxidation of activated and un‐activated aliphatic chains via in situ formation of methyl(trifluoromethyl)dioxirane (TFDO). The reported procedure demonstrated a broad scope and good functional‐group compatibility (28 examples, 8–99 %).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805657