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Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

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.

SUBMITTER: Yi J

PROVIDER: S-EPMC7086342 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Yi Jun J Badir Shorouk O SO Alam Rauful R Molander Gary A GA

Organic letters 20190530 12

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 r ...[more]

PMID: 31145628

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