Highly active alkyne metathesis catalysts operating under open air condition

Yanqing Ge, Shaofeng Huang, Yiming Hu, Lei Zhang, Ling He, Sebastian Krajewski, Michael Ortiz, Yinghua Jin and Wei Zhang ()
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Yanqing Ge: Shandong First Medical University & Shandong Academy of Medical Sciences
Shaofeng Huang: University of Colorado Boulder
Yiming Hu: University of Colorado Boulder
Lei Zhang: Sichuan University
Ling He: Sichuan University
Sebastian Krajewski: University of Colorado Boulder
Michael Ortiz: University of Colorado Boulder
Yinghua Jin: University of Colorado Boulder
Wei Zhang: University of Colorado Boulder

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: Abstract Alkyne metathesis represents a rapidly emerging synthetic method that has shown great potential in small molecule and polymer synthesis. However, its practical use has been impeded by the limited availability of user-friendly catalysts and their generally high moisture/air sensitivity. Herein, we report an alkyne metathesis catalyst system that can operate under open-air conditions with a broad substrate scope and excellent yields. These catalysts are composed of simple multidentate tris(2-hydroxyphenyl)methane ligands, which can be easily prepared in multi-gram scale. The catalyst substituted with electron withdrawing cyano groups exhibits the highest activity at room temperature with excellent functional group tolerance (-OH, -CHO, -NO2, pyridyl). More importantly, the catalyst provides excellent yields (typically >90%) in open air, comparable to those operating under argon. When dispersed in paraffin wax, the active catalyst can be stored on a benchtop under ambient conditions without any decrease in activity for one day (retain 88% after 3 days). This work opens many possibilities for developing highly active user-friendly alkyne metathesis catalysts that can function in open air.

Date: 2021
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DOI: 10.1038/s41467-021-21364-4

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