Affordable and atom-economical, gaseous reagents are frequently disregarded due to a combination of chemical and practical considerations. In contrast, this study showcases their facile applicability as versatile reagents within the realm of organic synthesis. The use of flow technology provides a robust, safe, and scalable platform for the HAT-activation of the volatile alkanes. Upon activation they form nucleophilic radicals that react with SO₂ to yield corresponding sulfinates. These sulfinates are versatile building blocks, opening new pathways for the synthesis of various sulphur-containing organic compounds such as sulfones, sulfonamides, and sulfonate esters.

Paper abstract

Sulphur-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 SO₂ to yield the corresponding sulfinates. These sulfinates then serve as versatile building blocks for the synthesis of diverse sulphur-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.

Paper details

Dmitrii Nagornîi, Fabian Raymenants, Nikolaos Kaplaneris & Timothy Noël: C(sp³)–H sulfinylation of light hydrocarbons with sulfur dioxide via hydrogen atom transfer photocatalysis in flow. Nat. Commun. 15, 5246 (2024). DOI: 10.1038/s41467-024-49322-w

See also

Website Flow Chemistry Research group