Issue 17, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
18 Dec 2015
Accepted
29 Jan 2016
First published
29 Jan 2016
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2016,52, 3520-3523

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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