Previously, our group has reported the photochemical oxidation of diaryl- and triarylamines to form carbazoles, but the existing methods fail to promote heterocycle formation when starting materials possess a free amine. In the current context of sustainable synthesis, the development of practical photochemical amination would be a welcome addition to the toolbox of synthetic chemists.<br/><br/>We have recently developed a photochemical continuous-flow synthesis of heterocycles using UV light. This methodology affords unprotected, free N-H, carbazoles, indoles and pyrroles. The use of low energy UV light, such as purple LED (394 nm), allow the formation of halogen containing carbazole, without deshalogenation of the desired product. In addition, we tested scale up strategies, numbering-out and numbering-up, in continuous-flow to improve the throughput of the reactor. Lastly, investigation of telescope reaction is on going to further functionalize the carbazole core.

Photochemical intramolecular amination for the synthesis of heterocycles

255th National Meeting (2018)

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