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Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates

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journal contribution
posted on 30.05.2019 by Jun Yi, Shorouk O. Badir, Rauful Alam, Gary A. Molander
A redox-neutral alkyl Petasis reaction has been developed that proceeds via photoredox catalysis. A diverse set of primary, secondary, and tertiary alkyltrifluoroborates participate effectively in this reaction through a single-electron transfer mechanism, in contrast to the traditional two-electron Petasis reaction, which accommodates only unsaturated boronic acids. This protocol is ideal to diversify benzyl-type and glyoxalate-derived aldehydes, anilines, and alkyltrifluoroborates toward the rapid assembly of libraries of higher molecular complexity important in pharmaceutical and agrochemical settings.