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Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates

Author:
Yi, Jun, Badir, Shorouk O., Alam, Rauful, Molander, Gary A.
Source:
Organic letters 2019 v.21 no.12 pp. 4853-4858
ISSN:
1523-7052
Subject:
agrochemicals, aldehydes, boronic acids, catalytic activity, chemical structure, redox reactions
Abstract:
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.
Agid:
6478233