New Strategies and Reactions for the α-C–H Functionalization and Hydrofunctionalization of Carbon–Carbon Multiple Bonds

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Project Summary The objective of this project is the development of a series of new organic methods through nontraditional approaches for the activation of the π-bonds of alkynes and alkenes, along with their associated propargylic and allylic positions. These methods greatly increase the versatility of these functional groups, providing streamlined access to substructures and motifs that regularly occur in compounds of relevance to biomedical research. In particular, in the first research area, we develop iron-based catalysts for the catalytic generation of nucleophilic propargyl and allyl equivalents. The production of these catalytic intermediates will allow for the formation of C–C and C–X bonds in a variety of synthetically useful and biomedically relevant contexts. In the second research area, we develop methods that take advantage of a newly discovered series for reagents and conditions for the generation of electron-deficient vinyl intermediates from alkynes. These reagents and conditions enable the development of vinyl electrophile chemistry in complex, late-stage contexts for the synthesis of heterocyclic derivatives and trisubstituted olefins in a stereodefined manner. These new methods will allow for drug discovery and development efforts to take place in an accelerated manner to exert a positive impact on public health.