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

Figures & data

Figure 1. Representative substrates explored for an EAS teaching lab experiment.

Scheme 1. Published teaching laboratory experiments using Oxone for an EAS reaction.

Scheme 2. Iodination of vanillin experiment investigating regioselectivity.

Scheme 3. Published Sonogashira coupling reaction using 5-iodovanillin ( 16, 17).

Scheme 4. Suzuki coupling of 5-iodovanillin with 4-methylphenylboronic acid experiment.

Figure 2. 5-Iodovanillin student product and ¹H NMR spectrum with inset of expanded aromatic region.

Figure 3. ¹H NMR spectrum of the Suzuki product with inset of expanded aromatic region.

Doxsee, K.M.; Hutchinson, J.E. Green Organic Chemistry - Strategies, Tools and Laboratory Experiments; Brooks-Cole: Pacific Grove, CA, 2004. pp 186–188.

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