Selective C-H functionalization of organic molecules has become increasingly important in streamlining organic synthesis. Methods to perform these reactions often involve transition metal catalysts. Orthogonally, radical chemistry provides a rich armament of reactions that are known to perform regioselective derivatizations including aminations. To advance the utility of these transformations beyond the present molecular frameworks, we have developed a chaperone that allows radical functionalizations when bound to alcohols – a common functional group in biologically active molecules. Installation of this chaperone can be done in situ using convenient and common reagents. Removal is operationally simple or the intermediate can be further derivatized to generate various analogs. By targeting alcohols with this tether, site-selective aminations are achieved in the presence of a wide variety of C-H bonds. Application of this synthetic method is demonstrated in the context of late-stage functionalization of drugs and natural products.

β C-H amination of alcohols via a radical relay chaperone

253rd National Meeting (2017)

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