Allenes have continuously attracted the attention of researchers for decades due to their presence in bioactive natural products and pharmaceuticals, unique geometry, and ability to transfer chirality. Allenes are also high value products in the medicinal chemistry community because they play key roles in the biological activity of numerous natural products, and serve as precursors to complex synthetic targets. As in other aspects of synthetic chemistry, many methods producing substituted allenes require the use of a precious metal catalyst such as palladium, iridium, and silver. While palladium catalysts in particular have made substantial contributions to synthetic chemistry, relying on precious metal catalysts is not only expensive, but unsustainable due to their low natural abundances. The field of transition metal catalysis has been moving toward investigating the use of first-row transition metals because of their the relatively high natural abundances and sustainability. These qualities make first-row elements attractive candidates for catalysis in comparison to the corresponding precious second- and third-row transition metals which currently dominate the field. We are particularly interested in looking into how palladium can be replaced with nickel, its first-row counterpart, in allene formation. This work focuses on the reactions of in-situ formed metallo-allenes with various nucleophilic compounds. This will enhance the field’s breadth and offer a more sustainable approach to allenic precursors for bioactive and synthetically interesting compounds.

Exploring nickel catalysis in allene synthesis

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.