Olefins are a common chemical feedstock, bench-stable, and tolerant of diverse reaction conditions, making them convenient functional groups to employ in organic synthesis. Metal-hydride hydrogen atom transfer (MHAT) is a catalysis manifold that has been used to convert unactivated olefins into hydrofunctionalized products with exquisite branched-to-linear selectivity. As a radical based transformation, MHAT has traditionally utilized stoichiometric radical traps (e.g. O<sub>2</sub>), which has limited the breadth of possible transformations.<br/><br/>Our lab has an interest in combining MHAT with nickel catalytic cycles to broaden the scope of available coupling partners. This work has resulted in the creation of novel branch-selective cross couplings. Recently, we have developed an Fe/Ni dual catalytic system which promotes the hydroarylation of mono-, di-, tri-, and tetrasubstituted olefins and provides access to a range of arylated quaternary centers. This method allows for simplified construction of pharmaceutically relevant cores bearing saturated motifs such as oxetanes and piperidines.

Quaternary centers via dual-catalytic alkene hydroarylation

2019 Fall National Meeting

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