Visible-light-initiated metal-free Csp3–Csp3 to Csp3–N conversion in homobenzylic sulfonamides with N-iodoimides

Guillermo Morales-Ortega; Estíbaliz Merino; Javier Carreras

doi:10.1039/D5SC02168E

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Visible-light-initiated metal-free C_sp³–C_sp³ to C_sp³–N conversion in homobenzylic sulfonamides with N-iodoimides†

Guillermo Morales-Ortega,

^ab Estíbaliz Merino

^ab and Javier Carreras

*^ab

Author affiliations

* Corresponding authors

^a Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, Alcalá de Henares, Madrid, Spain

^b Instituto Ramón y Cajal de Investigación Sanitaria (IRYCIS), Madrid 28034, Spain
E-mail: javier.carreras@uah.es

Abstract

We report a simple protocol for the transformation of C_sp³–C_sp³ to C_sp³–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.

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Article information

DOI: https://doi.org/10.1039/D5SC02168E
Article type: Edge Article
Submitted: 20 Mar 2025
Accepted: 16 May 2025
First published: 19 May 2025
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2025, Advance Article

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Visible-light-initiated metal-free C_sp³–C_sp³ to C_sp³–N conversion in homobenzylic sulfonamides with N-iodoimides

G. Morales-Ortega, E. Merino and J. Carreras, Chem. Sci., 2025, Advance Article , DOI: 10.1039/D5SC02168E

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