Highly Site-Selective Epoxidation of Polyene Catalyzed by Metal-Organic Frameworks Assisted by Polyoxometalate

Ectropis obliqua Prout is one of the most severe defoliator insects of tea plants. Sex pheromones method has been widely used for monitoring and controlling the insect pest of E. obliqua Prout due to their relative safety, low cost, and environmental friendliness. However, conventional preparing sex pheromones of E. obliqua Prout has been criticized by the costly and/or low efficiency procedure. Herein, we report a series of Fe-based metal-organic frameworks (MOFs) as efficient heterogeneous catalysts for the site-selective epoxidation of 3Z,6Z,9Z-octadecatriene to its monoepoxides. Particularly, MIL-100(Fe) combined with polyoxometalate (POM) as cocatalyst appears as the best catalyst for the oxidation of 3Z,6Z,9Z-octadecatriene to a high site selectivity to the corresponding 6,7-epoxide with good yields. 3Z,6Z,9Z-octadecatriene and its corresponding 6,7-epoxide are the primary sex pheromone components of the E. obliqua Prout. Significantly, the field bioassay experiments showed that the mixed products were highly effective in attracting E. obliqua Prout male moths. This work provides a general method to fast and clean synthesis of sex pheromones and opens new avenues for the application of Fe-based MOFs in the pest control with environmental friendliness.