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Issue 17, 2016
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Brønsted acid-catalysed conjugate addition of photochemically generated α-amino radicals to alkenylpyridines

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Abstract

The conjugate addition of α-amino radicals to alkenylpyridines has been accomplished by the synergistic merger of Brønsted acid and visible light photoredox catalysis. Key to reaction development was the protonation of the alkenylpyridines that transiently generated a highly reactive, electrophilic pseudo-iminium ion intermediate. Initial investigations using chiral phosphoric acids provide clues on the feasibility of an enantioselective catalytic variant.

Graphical abstract: Brønsted acid-catalysed conjugate addition of photochemically generated α-amino radicals to alkenylpyridines

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Publication details

The article was received on 18 Dec 2015, accepted on 29 Jan 2016 and first published on 29 Jan 2016


Article type: Communication
DOI: 10.1039/C5CC10401G
Chem. Commun., 2016,52, 3520-3523
  • Open access: Creative Commons BY-NC license
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    Brønsted acid-catalysed conjugate addition of photochemically generated α-amino radicals to alkenylpyridines

    H. B. Hepburn and P. Melchiorre, Chem. Commun., 2016, 52, 3520
    DOI: 10.1039/C5CC10401G

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