Coupling reactions are incredibly important transformations in organic synthesis, both in research and in medicinal chemistry. Current best coupling reactions, like Suzuki couplings and Sonogoshira couplings, are limited by their use of a Pd catalyst, which is costly and tends to perform poorly with sp<sup>3</sup> coupling partners. However, in over 30 years of research no reactions have been able to dethrone Suzuki couplings, or even Pd-catalyzed couplings in general. Within the last 10 years, first row transition metal catalysts have become attractive alternatives to traditional Pd-catalyzed couplings, but currently none are as robust as the Suzuki. This reality suggests that a fundamentally new reaction must be developed if the limits of current couplings are to be overcome. In this respect, organotetrafluorosilicates show promise as a new coupling partner. Initial results show that tetrafluorosilicates will couple with a halogenated electrophile in the presence of a Ni catalyst, leaving behind non-toxic and easily removable byproducts. Optimization and substrate scope of this new transformation will be discussed.

Nickel-catalyzed cross-coupling of ammonium organotetrafluorosilicates

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.