The difunctionalization of alkenes is a valuable synthetic tool to rapidly achieve molecular complexity in a single step. In particular, the hydroamination of olefins has been extensively investigated, as it allows for access to alkylamines, which are important pharmacophores. However, many hydroamination protocols utilize transition-metal catalysts and substrates are often limited to activated alkenes. As an orthogonal method to these approaches, we have developed a highly regioselective radical-mediated hydroamination of unactivated, non-polarized p-systems. The use of this chaperone strategy, which uses a labile directing group, is expanded to achieve vicinal functionalization of olefins.<br/>

Functionalization of allylic alcohols via a radical relay chaperone strategy

255th National Meeting (2018)

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