Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Org Lett

Roy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania, 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.

Published: June 2019

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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7086342PMC
http://dx.doi.org/10.1021/acs.orglett.9b01747DOI Listing

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