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

We report a simple protocol for the transformation of Csp3–Csp3 to Csp3–N in homobenzylic sulfonamides in combination with N-iodoimides to form gem-diamino derivatives. The reaction exhibits a wide functional group… Click to show full abstract

We report a simple protocol for the transformation of Csp3–Csp3 to Csp3–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.

Keywords: light initiated; homobenzylic sulfonamides; visible light; initiated metal; csp3 csp3; csp3

Journal Title: Chemical Science
Year Published: 2025

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