Iodination of vanillin and subsequent Suzuki-Miyaura coupling: two-step synthetic sequence teaching green chemistry principles

A two-step synthetic sequence using vanillin was developed for undergraduate organic chemistry labs to replace traditional experiments with greener alternatives. The first step involves iodinating vanillin with Oxone® and potassium iodide in refluxing water, enabling students to analyze substitution positions via ¹H NMR spectroscopy. The iodovanillin is then used in an aqueous Suzuki-Miyaura reaction with para-methylphenylboronic acid for a second ¹H NMR spectrum. This sequence, which can be conducted under conventional heating or microwave conditions, demonstrates green chemistry principles by utilizing a renewable feedstock, safer reagents, and water as a solvent while minimizing waste through the use of an intermediate product.

Full citation
Palesch, J. J., Gilles, B. C., Chycota, J., Haj, M. K., Fahnhorst, G. W., & Wissinger, J. E. (2019). Iodination of vanillin and subsequent Suzuki-Miyaura coupling: two-step synthetic sequence teaching green chemistry principles. Green Chemistry Letters and Reviews, 12(2), 117-126. https://doi.org/10.1080/17518253.2019.1609603