Green Multicomponent Reaction for the Organic Chemistry Laboratory. The Aqueous Passerini Reaction.
Date of Original Version
Water is the ideal green solvent for organic reactions. However, most organic molecules are insoluble in it. Herein, we report a laboratory module that takes advantage of this property. The Passerini reaction, a three-component coupling involving an isocyanide, aldehyde, and carboxylic acid, typically requires ~ 24 h reaction times in organic solvents, but produces a quantitative conversion and yield in < 30 min when performed in water. This rate enhancement allows the Passerini reaction to be easily adapted for use in a second-year organic laboratory course. Additionally, the incorporation of this laboratory module facilitates discussions of both green chemistry and combinatorial chemistry in the curriculum.
Hooper, M. M., & DeBoef, B. (2009). A Green Multicomponent Reaction for the Organic Chemistry Laboratory. The Aqueous Passerini in Reaction. Journal of Chemical Education, 86(9), 1077. doi: 10.1021/ed086p1077
Available at: http://dx.doi.org/10.1021/ed086p1077