Direct conversion from alkenes to alkynes

"Alkynes are widely used as feedstock chemicals and functional groups in organic chemistry. However, while the hydrogenation from an alkyne to an alkene is well established, typical methods for the reverse reaction—conversion of an alkene to an alkyne—are based on elimination chemistry reported in the 1860s and use forcing conditions (strong base or high temperatures)."

"Here we report a recyclable selenanthrene reagent that mediates alkenes desaturation to alkynes under mild conditions. This method shows broad compatibility with both classical leaving groups and sensitive functional groups, enabling application late-stage in the efficient synthesis of complex alkynes."

"Moreover, this platform enables Z/E alkenes configuration inversion or sorting that are inaccessible with existing methods, highlighting its potential for diverse downstream derivatizations."

Alkyne-to-alkene hydrogenation is well-established in organic chemistry, but the reverse reaction—converting alkenes to alkynes—relies on traditional elimination methods from the 1860s requiring harsh conditions like strong bases or high temperatures. These forcing conditions limit application to complex functional molecules. A new recyclable selenanthrene reagent mediates alkene desaturation to alkynes under mild conditions with broad compatibility for both classical and sensitive functional groups. This enables late-stage alkyne synthesis in complex molecule preparation. Additionally, the platform facilitates Z/E alkene configuration inversion or sorting, capabilities unavailable through existing methods, opening possibilities for diverse downstream chemical transformations.

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