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Metal-Free Generation of γ-Cyanoalkyl Radicals by N-Heterocyclic Carbene Catalysis: Assembly of 6-Cyanoalkyl Phenanthridines.

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A number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed by insertion into biaryl isonitriles, thus leading to the rapid assembly… Click to show full abstract

A number of γ-cyanoalkyl radicals were generated by sustainable N-heterocyclic carbene catalysis in tin-, transition-meal-, and light-free conditions, followed by insertion into biaryl isonitriles, thus leading to the rapid assembly of a variety of diversely functionalized 6-cyanoalkyl phenanthridines. A preliminary mechanism study revealed that a single-electron transfer radical process was possibly involved.

Keywords: cyanoalkyl radicals; cyanoalkyl phenanthridines; cyanoalkyl; heterocyclic carbene; carbene catalysis

Journal Title: Organic letters
Year Published: 2022

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