Uses
2,3-Dihydrofuran is a versatile reagent used in lanthanide-catalyzed Diels-Alder reactions with 2-pyrones and in Rh(II)-stabilized cycloadditions with vinylcarbenoids. It is applied for alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenyl-phosphine)-palladium(II). It is also used in the preparation of biologically active compounds such as antitumor agents.
Synthesis
2,3-Dihydrofuran is produced by the liquid-phase conversion of 1,4-butanediol over kaolin-supported Co–Cu catalysts, achieving yields up to 81% following reduction at 320 °C[2]. The compound is also synthesized via the cyclization of 1-alkyn-4-ols promoted by molybdenum pentacarbonyl-trimethylamine, or through transition-metal-free multi-functionalization of β-trifluoromethyl enones and azacycles[1][3].
References
[1] Hu, Y.-F., Han, W., Chen, Y.-K., Ma, M., Shen, Z.-L., & Chu, X.-Q. (2024). Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis. Organic Chemistry Frontiers : An International Journal of Organic Chemistry, 11 18, Pages 5144-5150. https://doi.org/10.1039/d4qo00962b
[2] Leite, L., Stonkus, V., Edolfa, K., Ilieva, L., Plyasova, L., & Zaikovskii, V. (2006). Copper-promoted cobalt catalysts for 2,3-dihydrofuran synthesis. Applied Catalysis A: General, 311, Pages 86-93. https://doi.org/10.1016/j.apcata.2006.06.006
[3] McDonald, F. E., Connolly, C. B., Gleason, M. M., Towne, T. B., & Treiber, K. D. (1993). A new synthesis of 2,3-dihydrofurans: cycloisomerization of alkynyl alcohols to endocyclic enol ethers. The Journal of Organic Chemistry, 58(25), 6952–6953. https://doi.org/10.1021/jo00077a006
