Accessing Molecular Complexity from Methane and Other Gaseous Alkanes via Photocatalytic Cascade Cyclization

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Abstract
The direct transformation of simple and abundant feedstocks into structurally complex molecules remains a central challenge in modern organic synthesis. Herein, we report a method for the oxidative cascade cyclization of N ‐aryl and N ‐benzoyl acrylamide derivatives, promoted by methane and other gaseous alkanes. This transformation is enabled by a readily available iron catalyst in combination with N ‐fluorobenzenesulfonimide (NFSI) as the oxidant, proceeding under mild conditions to afford a diverse array of N ‐heterocyclic frameworks in high yields. Late‐stage functionalization studies highlight the utility of methane in the synthesis of biologically relevant scaffolds. Moreover, the Fe/NFSI system facilitates a radical sampling regime that enables the selective functionalization of less reactive primary C─H bonds. Overall, this work establishes a sustainable and versatile platform for constructing molecular complexity directly from gaseous alkanes.
Funding Information
  • European Research Council (863914)
  • Agencia Estatal de Investigación (PID2023‐151875NB‐I00)
  • Xunta de Galicia (ED431C 2022/27)
  • Xunta de Galicia (ED431G 2023/03)

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