Gomberg–Bachmann C–H Arylation of Cyclic Nitrones Enabled by an Organic Base
We report the first direct C(sp<sup>2</sup>)-H functionalization of cyclic aldonitrones (namely 2<i>H</i>-/4<i>H</i>-imidazole <i>N</i>-oxides) using aryl diazonium tetrafluoroborates, with the process being solely promoted by <i>N</i>,<i>N</i>-diisopropylethylamine (DIPEA). This Gomberg-Bachmann-type protocol allowed 37 arylated nitrones to be obtained in 33-86% yields. A mechanistic study involving LCMS and EPR techniques has confirmed the radical essence of the approach, whereas the XRD analysis of some reaction products has revealed the unconventional π-hole tetrel bonding characteristic of their supramolecular arrangement.
Authors
- A. A. Pershin (ORCID: https://orcid.org/0000-0002-6630-6833)
- А. Ya. Tikhonov (ORCID: https://orcid.org/0000-0002-6391-4366)
- Alexey A. Akulov (ORCID: https://orcid.org/0000-0003-3966-3728)
- Mikhail V. Varaksin (ORCID: https://orcid.org/0000-0002-7997-3686)
- Dmitrii G. Mazhukin (ORCID: https://orcid.org/0000-0002-6915-6287)
- Anton N. Tsmokalyuk (ORCID: https://orcid.org/0000-0001-9333-4197)
- Олег Николаевич Чупахин (ORCID: https://orcid.org/0000-0002-1672-2476)
- Anastasia A. Deleva
- Mark V. Chugaev
Institutions
- Ural Federal University (RU)
- Novosibirsk Institute of Organic Chemistry (RU)
- Institute of Organic Synthesis (RU)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-11-21
- DOI
- https://doi.org/10.1021/acs.joc.5c02260
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94