2025, Publicación

Morales-Ortega et al. Chem Sci. ;:11413-11418. Visible-light-initiated metal-free C(sp(3)) -C(sp(3)) to C(sp(3)) -N conversion in homobenzylic sulfonamides with N-iodoimides.

Publications > Morales-Ortega et al

Chem Sci. 2025, 16, 11413-11418. doi: 10.1039/d5sc02168e. PubMed 40417292

Visible-light-initiated metal-free C(sp(3)) -C(sp(3)) to C(sp(3)) -N conversion in homobenzylic sulfonamides with N-iodoimides.

Guillermo Morales-Ortega1, Estíbaliz Merino2, a, Javier Carreras1

1. Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá Alcalá de Henares Madrid 28805 Spain.  2. Instituto Ramón y Cajal de Investigación Sanitaria (IRYCIS) Madrid 28034 Spain.

a. javier.carreras@uah.es

Abstract

We report a simple protocol for the transformation of C(sp(3)) -C(sp(3)) to C(sp(3)) -N in homobenzylic sulfonamides in combination with N-iodoimides to form gem-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.