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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Published inAngewandte Chemie International Edition Vol. 56; no. 36; pp. 10877 - 10880
Main Authors Hu, Rong‐Bin, Sun, Shuai, Su, Yijin
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 28.08.2017
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkenes
Bromides
Chemistry
Chemistry, Multidisciplinary
Light effects
nitrogen heterocycles
photochemistry
Physical Sciences
Pyridinium
radicals
reaction mechanisms
Salts
Science & Technology
DONOR-ACCEPTOR COMPLEX
radicals
reaction mechanisms
DRIVEN
alkenes
YLIDES
CATALYTIC FORMATION
CENTERED RADICALS
photochemistry
nitrogen heterocycles
1,3-DIPOLAR CYCLOADDITION
PHOTOCHEMICAL ACTIVITY
ALPHA-ALKYLATION
CHIRALITY
2+2 PHOTOCYCLOADDITION REACTIONS
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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.
Bibliography:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201704385