Dual Photoredox/Nickel‐Catalyzed Three‐Component Carbofunctionalization of Alkenes

The potential of merging photoredox and nickel catalysis to perform multicomponent alkene difunctionalizations under visible‐light irradiation is demonstrated here. Secondary and tertiary alkyl groups, as well as sulfonyl moieties can be added to the terminal position of the double bond with simulta...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-08, Vol.58 (35), p.12286-12290
Main Authors: García‐Domínguez, Andrés, Mondal, Rahul, Nevado, Cristina
Format: Article
Language:English
Subjects:
Additives
Alkenes
Catalysis
Functional groups
Irradiation
Light irradiation
multicomponent reactions
Nickel
photochemistry
Radiation
reaction mechanisms
Reagents
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Summary:The potential of merging photoredox and nickel catalysis to perform multicomponent alkene difunctionalizations under visible‐light irradiation is demonstrated here. Secondary and tertiary alkyl groups, as well as sulfonyl moieties can be added to the terminal position of the double bond with simultaneous arylation of the internal carbon atom in a single step under mild reaction conditions. The process, devoid of stoichiometric additives, benefits from the use of bench‐stable and easy‐to‐handle reagents, is operationally simple, and tolerates a wide variety of functional groups. A cut of π: Demonstrated here is the use of a dual Ru/Ni catalytic system in a three‐component carbofunctionalization of alkenes under visible‐light irradiation. The method allows the simultaneous and regiocontrolled addition of aromatic groups together with either sulfonyl or alkyl groups across the π system with readily available, bench‐top stable sulfinate and alkylsilicate partners.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201906692