Four membered carbo- and heterocycles are synthetically useful and prevalent motifs in chemical synthesis. Theoretically, they can be constructed through cycloadditions using simple alkenes, carbonyls, or imines. Despite the importance of these motifs in bioactive compounds there is a dearth of practical synthetic methodologies with a wide and general substrate scope. Current methodologies rely primarily on Ru/Ir/Rh photocatalysts and require multi-point coordination of the substrate, greatly limiting the scope of such transformations. To expand this chemical space, we have developed a Cu-based precatalyst that activates substrates to partake in the desired photocycloadditions. Mechanistically this is fundamentally different from traditional photocycloadditions, operating under new modes of substrate activation.

Copper mediated photochemical cycloadditions for the synthesis of small heterocycles

2019 Fall National Meeting

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