A method for sulfonic acid functionalized metal-organic framework material to catalyze cross-dehydrogenation coupling reaction
A cross-dehydrogenation coupling and metal-organic framework technology, applied in catalytic reactions, organic chemistry, organic compound/hydride/coordination complex catalysts, etc., to avoid pre-functionalization steps, high reaction atom economy, cost high effect
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Embodiment 1
[0056] Optimization of reaction conditions:
[0057] MIL-101(Cr)-SO 3 The H-catalyzed coupling reaction of xanthene and cyclopentanone is a model reaction, and the reaction conditions are optimized. The reaction steps are as follows: add xanthene (1 equiv), different amounts of MIL-101(Cr)-SO 3 H (1 mol%-15 mol%), cyclopentanone (5 equiv). After purging the reaction bottle with oxygen flow to remove air, seal the reaction tube, insert an oxygen balloon, and stir and react at 40°C for 24h. After the reaction, the solid catalyst was separated by centrifugation, the solid was washed three times with solvent, the combined solution was evaporated to remove the solvent under reduced pressure, and the concentrate was separated by column chromatography (petroleum ether / ethyl acetate as eluent) to obtain C-C coupling product 3.
[0058] The dehydrogenation cross-coupling reaction of xanthene 1 and ketone 2 to obtain the C-C coupling product is as follows:
[0059]
[0060] The y...
Embodiment 2
[0068] A method for the CDC reaction of MOFs catalyzed xanthenes and ketones, the specific steps are as follows:
[0069] In the reaction tube, add xanthene (0.2mmol), MIL-101(Cr)-SO 3 H (5 mol%), cyclohexanone (5 equiv). After purging the reaction bottle with oxygen flow to remove air, seal the reaction tube, insert an oxygen balloon, and stir and react at 40°C for 24h. After the reaction, the solid catalyst was centrifuged, the solid was washed 3 times with a solvent, the combined solution was evaporated under reduced pressure to remove the solvent, and the concentrate was separated by column chromatography (petroleum ether / ethyl acetate as eluent) to obtain the C-C coupling product (±)- 9-(1'-oxo-2'-cyclohexyl)xanthene, the yield is 91%.
Embodiment 3-11
[0071] A method for MOFs catalyzing the reaction of xanthene and nucleophile CDC, its specific steps are the same as in Example 2, and its different parts use different nucleophiles to obtain the structures and yields of different coupling products as shown in Table 2 . The general reaction formula is as follows:
[0072]
[0073] Table 2 The structure and yield of the coupling products of xanthene and different nucleophiles
[0074]
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