Yu, Z., Xu, F., Li, Y., Konno, H., Li, H., & Yang, S. (2019). Current Green Chemistry, 6(2), 127-134.
Hydrogenation of furfural (FUR) to furfuryl alcohol (FFA) is one of the key steps and representative examples of comprehensive utilization of biomass. Using molecular hydrogen, formic acid or alcohol as H donors usually requires relatively stringent conditions to obtain satisfactory results on expensive metal catalysts. In this work, a new benign reaction system consisting of green and cheap tetraethylammonium fluoride (TEAF) and polymethylhydrosiloxane (PMHS) was developed, which can effectively transfer the hydrogenation of biological FUR to high value FFA under mild conditions.
Reaction Mechanism
The possible reaction mechanism is based on the combination of FUR and hydrosilane.
1. First, the dissociated fluorine ions attack the silicon atoms bonded to the hydrogen anions of PMHS.
2. Then, under the activation of fluoride ion, the hydrogen anion reacts with the electron-deficient carbon atom in the carbonyl group, while the charged oxygen atom attacks the silicon atom to form a strong silicon-oxygen bond and releases fluoride ion to complete the catalytic cycle.
3. Finally, in the presence of water, the Si-O bond of the silicon-based intermediate was broken to obtain the target product alcohol.
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