Recently, we reported a room temperature and transition metal-free aryl-aryl cross coupling of several (hetero) arenes, under UV irradiation. At the time, we documented the synthesis of an interleukin-2 cytokine inhibitor as evidence of the synthetic utility of our method, albeit in couple of synthetic steps. This time, we are presenting the second-generation approach where we are now able to prepare this immunosuppressant (see the figure) in one pot procedure. The strategy involves two major transformations (aryl-aryl cross coupling and amidation reaction) occurring simultaneously. To the best of our knowledge, this work represents the first novel approach of two of the most useful transformations performed under mild/greener reaction conditions. Furthermore, it is a unique report on the use of natural sunlight to promote the title transformations. Therefore, this work and mechanistic insights can potentially open a new area of research to aid drug discovery.

Are aryl-aryl cross couplings and amidation reactions feasible and compatible under sunlight irradiation?

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.