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

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JournalACS Catalysis
DateAccepted/In press - 26 Nov 2018
DateE-pub ahead of print - 26 Nov 2018
DatePublished (current) - 4 Jan 2019
Issue number1
Volume9
Number of pages6
Pages (from-to)236-241
Early online date26/11/18
Original languageEnglish

Abstract

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.

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© 2018 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

    Research areas

  • deamination, dicarbofunctionalization, photoredox catalysis, redox-active, visible-light

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