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C(sp 3 )-H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow.

Dmitrii NagornîiFabian RaymenantsNikolaos KaplanerisTimothy Noël
Published in: Nature communications (2024)
Sulfur-containing scaffolds originating from small alkyl fragments play a crucial role in various pharmaceuticals, agrochemicals, and materials. Nonetheless, their synthesis using conventional methods presents significant challenges. In this study, we introduce a practical and efficient approach that harnesses hydrogen atom transfer photocatalysis to activate volatile alkanes, such as isobutane, butane, propane, ethane, and methane. Subsequently, these nucleophilic radicals react with SO 2 to yield the corresponding sulfinates. These sulfinates then serve as versatile building blocks for the synthesis of diverse sulfur-containing organic compounds, including sulfones, sulfonamides, and sulfonate esters. Our use of flow technology offers a robust, safe and scalable platform for effectively activating these challenging gaseous alkanes, facilitating their transformation into valuable sulfinates.
Keyphrases
  • visible light
  • electron transfer
  • molecular dynamics
  • signaling pathway
  • high throughput
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  • gas chromatography
  • single cell
  • simultaneous determination
  • tandem mass spectrometry