Jeffrey Quesnel is a senior graduate student in the group of Bruce Arndtsen. He won the 2014 Udho Parsini Diwan Prize, an award given to the graduate student authoring the most exciting research article in the past year in the Department. Jeff summarizes below the importance of his article, "A Palladium-Catalyzed Carbonylation Approach to Acid Chloride Synthesis", published in the Journal of the American Chemical Society (J. Am. Chem. Soc., 2013, 135 (45), 16841–16844).
Chemists often rely on the use of highly reactive starting materials to provide easy pathways to generate targeted products. While functional, this is often inefficient as the price paid is usually in the large amount of waste generated. As an example, acid chlorides, are typically made from chlorinating reagents. This is problematic because these chlorinating reagents are highly reactive and create stoichiometric byproducts, which must be neutralized and disposed of. A recent finding in our lab is these acid chlorides can be cleanly generated using a palladium catalyst from three very accessible components: aryl halides, CO, a 100% atom economical source of carbon, and a simple chloride salt. From this work, we identified the key features required for this three-component reaction. Importantly, the products of the reaction (acid chlorides) are themselves very reactive and they can be easily transformed into other useful products for organic synthesis. This reaction platform is easily adaptable and our group is currently combining this phenomenon with other types of metal-catalyzed transformations in our pursuit of more efficient ways to assemble molecules.