Optimizing catalyst reactivity, separation, and recycle in processes involving the palladium-catalyzed Suzuki coupling of heteroaromatic compounds
Senter, James C.
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Suzuki coupling is a transition-metal catalyzed reaction of an aryl halide and a boronic acid that forms carbon-carbon bonds. Due to its versatility, the Suzuki reaction has emerged as an important reaction in industrial synthesis. Nitrogen-containing compounds are important building blocks in many biological and pharmaceutical compounds; unfortunately, Suzuki reactions involving substrates with basic, nitrogen centers often obtain poor yields. Additionally, separation of reaction products from catalyst and recycling of said catalyst following reaction is difficult. These results are attributed to the coordination of these nitrogen moieties to the metal catalyst. Though techniques to overcome these limitations exist, they are often cost prohibitive. This work covers novel, Smart-Solvent techniques for improving reaction efficiency, separating Pd-catalyst from reaction products, and recycling the separated catalyst for Suzuki systems involving basic, nitrogen-containing substrates.