Sanna Stenfors: Derivatization of lignin-derived aldehydes towards value-added products
University of Jyväskylä
The central idea of my research is to utilize lignin-derived aldehydes for reconstruction of the carbon backbone of value-added products. These functionalized “2nd generation” building blocks can be useful, for example, in material chemistry or the production of pharmaceuticals. Lignin-derived aldehydes are highly versatile intermediates for further chemical transformations, like condensations, that offer a sustainable starting point for the preparation of valuable, functional molecules.
Most of my doctoral work so far has focused on the Favorskii reaction. It is an alkynylation reaction of carbonyl compounds, which forms propargyl alcohol products 4 as terminal alkynes 1 and stoichiometrically strong bases react with carbonyl compounds 2.1 In other words, Favorskii is strategically valuable way to form the new C-C- bond between alkyne 1 and aldehyde 2. The Favorskii reaction is based on the principles of carboxylate and probase catalysis, presented in Anton Bannykh's doctoral thesis, in which the activation of alkynes is achieved under metal-free and relatively mild conditions.2
In Favorskii, the combination of tetramethylammonium pivalate (TMAP) catalyst and neutral silylating agent N,O–bis(trimethylsilyl)acetamide (BSA) has proved to be an efficient catalytic system.3 This approach offers good functional group tolerance and reduces the need for reactive organometallic reagents. Overall, the research can combine the Favorskii reaction with organocatalytic thinking and expand its applicability to sustainable lignin chemistry.
References:
- Danilkina, N. A.; Vasileva, A. A. ja Balova, I. A., A.E. Favorskii’s scientific legacy in modern organic chemistry: prototropic acetylene – allene isomerization and the acetylene zipper reaction, Russ. Chem. Rev., 2020, 89, 125.
- Bannykh, A., From carboxylate catalysis to probase catalysis, 2025.
- Bannykh, A. ja Pihko, P. M., Carboxylate-Catalyzed C-Silylation of Terminal Alkynes, Org. Lett., 2024, 26, 1991–1995.