Palladium-Catalyzed Synthesis of a Benzofuran: a case study in the development of a green chemistry laboratory experiment

A well-recognized principle of green chemistry is the use of catalysis to effect chemical transformations. It is difficult, perhaps even impossible to find a current issue of a chemical journal that does not present the use of catalysis, with reports of metathesis-type reactions and of palladium-catalyzed transformations particularly prevalent. Despite the ubiquity of palladium-catalyzed reactions in the practice of synthetic chemistry, however, it is uncommon to find examples of palladium catalysis in the undergraduate laboratory curriculum. In this article, we present our development of such an experiment, beginning from its conception and discussing the progression of modifications and improvements required to convert a reaction as reported in the primary chemical literature to a procedure suitable for the undergraduate organic chemistry laboratory. This presentation, while focused on the development of a laboratory teaching module, serves to illustrate more generally the concepts, principles, and decision-making involved in the practice of green chemistry.