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Light and nickel catalysts remodel fused rings into sulfur-containing molecules

A peer-reviewed organic chemistry experiment rebuilt fused molecular rings into gamma-sultones using light-driven and nickel catalysis. The method worked across several starting structures and allowed further changes to the products, although some substrates produced mixtures. Early screening against the pinewood nematode found activity in selected compounds; field effectiveness and environmental safety were not established.

Science··Midday
A capped glass vial held by a clamp sits on a stirrer while a nearby blue LED panel illuminates it.

Rebuilding rings through light-driven chemistry

Light-driven catalysis combined with a nickel catalyst converted fused molecular rings into gamma-sultones, ring structures containing sulfur and oxygen. The peer-reviewed organic chemistry study reorganized the molecular skeleton rather than simply attaching a new group to its surface. Blue light powered the reaction at room temperature. Under the optimized conditions, the model product was isolated in 91% yield, giving a starting point for testing how widely the transformation could be used.[1]

A useful range, with competing reactions

The method worked with several ring sizes and substituted starting materials, including structures prepared from natural products and pharmaceuticals. Results varied across that range: some substrates gave lower yields or competing cyclization products, and certain internal alkynes produced mixtures. The resulting molecules retained an aldehyde group that could be changed in further reactions. This increased the variety of chemical structures available for investigation, without establishing that modified drug-derived molecules retain the biological effects of their starting compounds.[1]

Nematode screening remains a laboratory lead

An early biological screen tested selected products against the pinewood nematode, a microscopic worm associated with pine disease. Several showed activity. One compound killed all tested nematodes at the screening concentration, but a dose-response comparison found it less potent than the avermectin control. These controlled laboratory assays indicate a possible direction for further chemical work. They did not establish effectiveness in forests, environmental safety or a usable treatment for infested trees.[1]

References

  1. News sourceNature CommunicationsLight-assisted chemistry remodels rings into sulfur-containing structures↩1↩2↩3