Palladium-catalyzed Suzuki-Miyaura cross-couplings are widely employed reactions for the synthesis of complex biaryl molecules, including pharmaceuticals and agrochemicals. However, a longstanding challenge in this field is the development of methods that require low loadings of palladium to enable cost efficient and sustainable processes, especially at industrial scales. We hypothesize a key limitation when moving towards lower loadings of palladium is the efficiency of activation of the Pd(II) pre-catalysts commonly used to introduce reactive Pd(0) species as the active catalysts in these transformations. This work discusses the key challenges for lowering the catalyst loading in Pd-catalyzed cross-coupling reactions of highly functionalized molecules such as aminopyralid derivatives. The impact of ligand, pre-catalyst, impurity profile, and various functional groups on reaction rates and catalyst speciation will be described. Ultimately, this work will enable the design of highly activated Pd(II) pre-catalysts to efficiently conduct cross-coupling reactions of complex molecules at ppm levels of palladium.

Suzuki-Miyaura cross-couplings at low loadings of Pd

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