General Paradigm in Photoredox Nickel‐Catalyzed Cross‐Coupling Allows for Light‐Free Access to Reactivity

Self‐sustained NiI/III cycles are established as a potentially general paradigm in photoredox Ni‐catalyzed carbon–heteroatom cross‐coupling reactions through a strategy that allows us to recapitulate photoredox‐like reactivity in the absence of light across a wide range of substrates in the aminatio...

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Published inAngewandte Chemie International Edition Vol. 59; no. 24; pp. 9527 - 9533
Main Authors Sun, Rui, Qin, Yangzhong, Nocera, Daniel G.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.06.2020
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amination
Aromatic compounds
Bromides
Catalysis
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Cross coupling
Esterification
green chemistry
Nickel
photoredox catalysis
Physical Sciences
Science & Technology
Substrates
sustainable chemistry
transition metals
AMINATION
MECHANISM
transition metals
ARYL HALIDES
COMPLEXES
cross-coupling
photoredox catalysis
sustainable chemistry
MONOPHOSPHINE LIGANDS
OXIDATIVE ADDITION
green chemistry
ELECTROPHILES
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Summary:Self‐sustained NiI/III cycles are established as a potentially general paradigm in photoredox Ni‐catalyzed carbon–heteroatom cross‐coupling reactions through a strategy that allows us to recapitulate photoredox‐like reactivity in the absence of light across a wide range of substrates in the amination, etherification, and esterification of aryl bromides, the latter of which has remained, hitherto, elusive under thermal Ni catalysis. Moreover, the accessibility of esterification in the absence of light is especially notable because previous mechanistic studies on this transformation under photoredox conditions have unanimously invoked energy‐transfer‐mediated pathways. Turning the light off: Self‐sustained NiI/III cycles are established as a potentially general paradigm in photoredox cross‐coupling reactions. It is shown that photoredox‐like reactivity can be recapitulated with high fidelity in the complete absence of light across multiple substrates and transformations, thus obviating the need for high‐energy photons and precious‐metal photocatalysts.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201916398