Direct Oxidation of Csp 3 −H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

Abstract A fast, scalable, and safer C sp 3 −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 Csp 3 −H bon...

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Published inChemistry : a European journal Vol. 25; no. 5; pp. 1203 - 1207
Main Authors Lesieur, Mathieu, Battilocchio, Claudio, Labes, Ricardo, Jacq, Jérôme, Genicot, Christophe, Ley, Steven V., Pasau, Patrick
Format Journal Article
LanguageEnglish
Published 24.01.2019
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Summary:Abstract A fast, scalable, and safer C sp 3 −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 Csp 3 −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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201805657