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Red-Light-Promoted Radical Cascade Reaction to Access Tetralins and Dialins Enabled by Zinc(II)porphyrin, A Light-Flexible Catalyst.
Organic Letters 2024 April 27
[5,15-Bis(pentafluorophenyl)-10,20-diphenylporphinato]zinc(II) ( 1 ), a metalloporphyrin derivative that was recently reported as an efficient photocatalyst driven by blue LEDs by our group, was found to catalyze a red-light-promoted (630 nm LEDs) radical cascade reaction of N -3-arylpropionyloxyphthalimides with radicophiles including electron-deficient alkenes and alkynes, providing access to a range of functionalized tetralin and dialin derivatives. The radical cascade reaction catalyzed by 1 took place via an oxidative quenching cycle in DMSO, where no sacrificial electron donor was required, uncovering a unique solvent effect capable of promoting the porphyrin catalysis.
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