Nickel‐Catalyzed Reductive Alkylation of Heteroaryl Imines

The preparation of heterobenzylic amines by a Ni‐catalyzed reductive cross‐coupling between heteroaryl imines and C(sp3) electrophiles is reported. This umpolung‐type alkylation proceeds under mild conditions, avoids the pre‐generation of organometallic reagents, and exhibits good functional group t...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-09, Vol.61 (38), p.e202207597-n/a
Main Authors: Turro, Raymond F., Brandstätter, Marco, Reisman, Sarah E.
Format: Article
Language:English
Subjects:
Alkylation
Amines
Cross coupling
Electrochemistry
Functional groups
Imines
Nickel
Nickel-Catalysis
Reagents
Reductive alkylation
Substrates
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Summary:The preparation of heterobenzylic amines by a Ni‐catalyzed reductive cross‐coupling between heteroaryl imines and C(sp3) electrophiles is reported. This umpolung‐type alkylation proceeds under mild conditions, avoids the pre‐generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox‐active ligand upon coordination to a low‐valent Ni center. The resulting bis(2‐imino)heterocycle⋅Ni complexes can engage in alkylation reactions with a variety of C(sp3) electrophiles, giving heterobenzylic amine products in good yields. A Ni‐catalyzed reductive cross‐coupling of heteroaryl imines with C(sp3) electrophiles for the preparation of heterobenzylic amines is reported. Mechanistic studies are consistent with the imine substrate acting as a redox‐active ligand upon coordination to a low‐valent Ni center.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202207597