Visible-Light-Mediated Deaminative Three-Component Dicarbofunctionalization of Styrenes with Benzylic Radicals

The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational de...

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Bibliographic Details
Published in:ACS catalysis 2019-01, Vol.9 (1), p.236-241
Main Authors: Klauck, Felix J. R, Yoon, Hyung, James, Michael J, Lautens, Mark, Glorius, Frank
Format: Article
Language:English
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Summary:The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational design and use of benzylic pyridinium salts as radical precursors. Using this approach, abundant styrenes, electron-rich heterocycles, and benzylic amines were combined to rapidly afford a number of densely functionalized 1,1-diarylalkanes. A dipeptide-derived pyridinium salt was applied in this transformation, which resembles a visible-light-mediated deaminative generation of radicals from peptides.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b04191