Photomediated C–H trifluoromethoxylations enabled by bis(trifluoromethyl)peroxide
We describe a photomediated protocol for the trifluoromethoxylation of benzylic, aldehydic, and non-activated C-H bonds, using bis(trifluoromethyl)peroxide (BTMP, (F<sub>3</sub>CO)<sub>2</sub>) as the key reagent. Under catalyst-free conditions in acetone, this reaction proceeds with selective functionalization of benzylic methylene groups. Furthermore, by using tetrabutylammonium decatungstate as a photocatalyst, the scope extends to include both non-activated methylene C(sp<sup>3</sup>)-H and formyl C(sp<sup>2</sup>)-H bonds. The methodology was successfully applied to 24 examples including odorants, pharmaceuticals, and natural products and was demonstrated on gram scale. Finally, by using [<sup>13</sup>C]-BTMP, the corresponding trifluoromethoxy groups can be site-specifically labeled with <sup>13</sup>C.
Authors
- Manuela Weber (ORCID: https://orcid.org/0000-0002-2767-8933)
- Thomas Drews
- Mathias Christmann (ORCID: https://orcid.org/0000-0001-9313-2392)
- Sebastian Riedel (ORCID: https://orcid.org/0000-0003-4552-5719)
- Paul Golz (ORCID: https://orcid.org/0000-0002-6003-3109)
- Merlin Kleoff (ORCID: https://orcid.org/0000-0001-7350-542X)
- Kamar Shakeri
Institutions
- Freie Universität Berlin (DE)
Publication Details
- Journal
- Chemical Science
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5sc04945h
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- Newcastle University
- Freie Universität Berlin