Sulfonyl fluorides are gaining a wide use as chemical biology warheads for the exploration of protein active sites through covalent binding modes. In an effort to expand the available synthetic space around these important functional groups Medicinal Chemistry at Pfizer has teamed up with the Willis lab at the University of Oxford to explore the synthesis of vinyl sulfinates as versatile synthetic intermediates to access a wide variety of reactions and products. A series of low molecular weight, compact and multifunctional cyclic alkenylsulfonyl fluorides are efficiently prepared from the corresponding alkenyl triflates under the action of palladium catalysis. A range of functional groups can be tolerated, and a correspondingly large range of derivatization reactions are possible, including substitution at sulfur, conjugate addition, and N-functionalization. This talk will describe the ongoing collaborative synthetic work towards the preparation of these vinyl sulfonyl fluorides as multifunctional tools for synthesis and chemical biology.

Pd-catalyzed preparation cyclic alkenylsulfonyl fluorides: New motif for sulfur fluoride exchange

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.