Visible-light-initiated metal-free C<sub>sp<sup>3</sup></sub>–C<sub>sp<sup>3</sup></sub> to C<sub>sp<sup>3</sup></sub>–N conversion in homobenzylic sulfonamides with <i>N</i>-iodoimides
We report a simple protocol for the transformation of C<sub>sp<sup>3</sup></sub> -C<sub>sp<sup>3</sup></sub> to C<sub>sp<sup>3</sup></sub> -N in homobenzylic sulfonamides in combination with <i>N</i>-iodoimides to form <i>gem</i>-diamino derivatives. The reaction exhibits a wide functional group tolerance and allows the incorporation of bioactive-derived fragments. The mechanistic insights provided by control experiments and DFT calculations suggest that an imine intermediate is formed after C-C bond cleavage.
Authors
- Javier Carreras (ORCID: https://orcid.org/0000-0002-1521-6758)
- Estı́baliz Merino (ORCID: https://orcid.org/0000-0002-2960-5404)
- Guillermo Morales-Ortega (ORCID: https://orcid.org/0009-0008-7786-2801)
Institutions
- Universidad de Alcalá (ES)
- Instituto Ramón y Cajal de Investigación Sanitaria (ES)
Publication Details
- Journal
- Chemical Science
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5sc02168e
- Citations
- 1
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Comunidad de Madrid
- Ministerio de Ciencia, Innovación y Universidades
- Universidad de Alcalá
- Universidad de Zaragoza
- Instituto de Salud Carlos III
- Agencia Estatal de Investigación