Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen‐Atom Transfer, and Cobalt Catalysis

A synergistic catalytic method combining photoredox catalysis, hydrogen‐atom transfer, and proton‐reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditi...

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Bibliographic Details
Published in:Angewandte Chemie 2019-08, Vol.131 (32), p.11057-11061
Main Authors: Yu, Wan‐Lei, Luo, Yong‐Chun, Yan, Lei, Liu, Dan, Wang, Zhu‐Yin, Xu, Peng‐Fei
Format: Article
Language:English
Subjects:
Alkenes
Allylverbindungen
Atom economy
Catalysis
Chemistry
Cobalt
Dehydrogenation
Oxidants
Oxidizing agents
Photochemie
Photoredox catalysis
Radikale
Reaction mechanisms
Substitutes
Wasserstoffatomtransfer
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Summary:A synergistic catalytic method combining photoredox catalysis, hydrogen‐atom transfer, and proton‐reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditions without using oxidants. This transformation features good to excellent yields, operational simplicity, and high atom economy. Based on control experiments, a possible reaction mechanism is proposed. Eine synergistische Katalyse aus Photoredoxkatalyse, Wasserstoffatomtransfer und Protonenreduktionskatalyse ermöglicht die dehydrierende Silylierung von Alkenen. Die Reaktion zeichnet sich durch eine hohe Regioselektivität, ausgezeichnete Toleranz gegenüber funktionellen Gruppen und milde Reaktionsbedingungen aus. Darüber hinaus ist dieses oxidationsmittelfreie System effizienter als herkömmliche Katalysen, die stöchiometrische oder überschüssige Mengen an Oxidantien erfordern.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201904707