In the Minisci reaction, electron-deficient aromatic aza-heterocycles are readily functionalized by nucleophilic radicals, which are derived by silver-catalyzed oxidation of carboxylic acids. This reaction has inspired many related methods in recent years. Generally, these methods involve loss of the functional group required for free-radical generation. We have developed a new variant of this reaction that exploits the silver catalyzed silver cleavage of cyclopropanols to b-keto radicals, providing functionalized heterocycles with a ketone functional group handle for further elaboration. This study also revealed some mechanistic insights that may prove useful in other silver-catalyzed processes.

Functionalization of aromatic nitrogen heterocycles with cyclopropanols: The cyclopropanol Minisci reaction

256th National Meeting (2018)

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