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Cobalt-Catalyzed Cross-Coupling Reactions of Bench-Stable Zinc Reagents

Transition-metal-catalyzed cross-coupling reactions are indispensable tools for the construction of carbon-carbon bonds, which is of great importance for the synthesis of pharmaceuticals and agrochemicals. Boron organometallics have been extensively used for such reactions in medicinal chemistry, due to their broad availability and air- and moisture-stability, however many boronic esters have genotoxic properties which make their manipulations on an industrial scale especially difficult. In comparison, organozinc reagents display an excellent functional group compatibility and a better reactivity in coupling reactions. One of the most prominent applications for organozinc reagents is their use for the so-called Negishi cross-coupling, which earned its discoverer a share of the Nobel Prize for Chemistry in 2010. Most of these reactions are catalyzed by palladium or nickel; however, these metals have the disadvantage of toxicity and/or high costs. In contrast, cobalt salts are an inexpensive and less toxic alternative for carbon-carbon bond forming reactions.

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