Visible‐Light‐Induced Carbo‐2‐pyridylation of Electron‐Deficient Alkenes with Pyridinium Salts

A simple and practical visible‐light‐induced carbo‐2‐pyridylation of electron‐deficient alkenes with readily available N‐benzoylmethylpyridinium bromides is reported. More than 40 examples are presented and proceed in greater than 80 % yield (on average) with excellent regio‐ and diastereoselectivit...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-08, Vol.56 (36), p.10877-10880
Main Authors: Hu, Rong‐Bin, Sun, Shuai, Su, Yijin
Format: Article
Language:English
Subjects:
Alkenes
Bromides
Light effects
nitrogen heterocycles
photochemistry
Pyridinium
radicals
reaction mechanisms
Salts
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Summary:A simple and practical visible‐light‐induced carbo‐2‐pyridylation of electron‐deficient alkenes with readily available N‐benzoylmethylpyridinium bromides is reported. More than 40 examples are presented and proceed in greater than 80 % yield (on average) with excellent regio‐ and diastereoselectivities. Doubly radical! The generation of a biradical by a visible‐light‐induced intramolecular electron transfer process allows a carbo‐2‐pyridylation reaction of electron‐deficient alkenes using N‐benzoylmethylpyridinium bromides. More than 40 examples are presented and proceed in greater than 80 % yield (on average) with excellent regio‐ and diastereoselectivities. EWG=electron‐withdrawing group.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201704385