Fig. 4: Three-component direct radical addition—dearomative difunctionalization through spirocyclization. | Nature Communications

Fig. 4: Three-component direct radical addition—dearomative difunctionalization through spirocyclization.

From: Visible light-mediated dearomative spirocyclization/imination of nonactivated arenes through energy transfer catalysis

Fig. 4

Reaction conditions: oxime carbonate 4 (0.3 mmol, 1.5 equiv.), acrylamide 2 (0.2 mmol, 1.0 equiv.), non-activated alkene 5 (0.4 mmol, 2.0 equiv.), [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) (0.5 mol%), EtOAc (3 mL), N2, blue LEDs (440 nm, 10 W), 4 h, fan cooling (35–40 °C). Diastereomeric ratios were determined by 1H NMR spectroscopy. Bottom: Scope of the hydrogen atom transfer—dearomative difunctionalization through spirocyclization. Reaction conditions: oxime carbonate 4 (0.4 mmol, 1.5 equiv.), acrylamide 2 (0.2 mmol, 1.0 equiv.), aliphatic substrate 7 (2 mL), [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) (0.5 mol%), EtOAc (1 mL), N2, blue LEDs (440 nm, 10 W), 4 h, fan cooling (35–40 °C). Diastereomeric ratios were determined by 1H NMR spectroscopy. a benzaldehyde (1 mL), EtOAc (2 mL).

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