4.6 Article

Photoredox-Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4-Dihydropyridine Approach

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 37, Pages 8239-8243

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002410

Keywords

1; 4-dihydropyridines; carbamoyl radicals; Giese reaction; organic dyes; photoredox catalysis

Funding

  1. University of Hamburg
  2. Alexander von Humboldt Foundation

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Functionalization with C1-building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C-1-molecule, carbon dioxide, makes alternative carboxylation reactions with CO2-surrogates especially important. We report a photoredox-catalyzed protocol for alkene carbamoylations. Readily accessible 4-carboxamido-Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light-mediated single-electron transfer. Addition to various alkenes proceeded with high levels of regio- and chemoselectivity.

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