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

Accepted version
Peer-reviewed

Repository URI

https://www.repository.cam.ac.uk/handle/1810/287439

Repository DOI

https://doi.org/10.17863/CAM.34742
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Accepted version (1.16 MB)

Type

Article

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Authors

Lesieur, Mathieu  ORCID logo  https://orcid.org/0000-0002-7848-5111
Battilocchio, Claudio  ORCID logo  https://orcid.org/0000-0002-4601-8527
Labes, Ricardo  ORCID logo  https://orcid.org/0000-0003-4001-0775

Abstract

A fast, scalable, and safer Csp 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 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.

Description

Keywords

Oxone, TFDO, dioxirane, flow, hydroxylation, oxidation

Journal Title

Chemistry

Conference Name

Journal ISSN

0947-6539
1521-3765

Volume Title

25

Publisher

Wiley

Publisher DOI

https://doi.org/10.1002/chem.201805657

Rights and licensing

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Except where otherwised noted, this item's license is described as http://www.rioxx.net/licenses/all-rights-reserved
Sponsorship
The authors gratefully acknowledge the Walloon region (Bel-gium)-DG06 (Convention no. 7240) for funding

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University of Cambridge Research Outputs (Articles and Conferences)