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Direct Oxidation of Csp 3 −H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow
Author(s) -
Lesieur Mathieu,
Battilocchio Claudio,
Labes Ricardo,
Jacq Jérôme,
Genicot Christophe,
Ley Steven V.,
Pasau Patrick
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.201805657
Subject(s) - dioxirane , trifluoromethyl , chemistry , adamantane , in situ , continuous flow , reactivity (psychology) , functional group , combinatorial chemistry , organic chemistry , physics , mechanics , alkyl , medicine , alternative medicine , pathology , polymer
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.