Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 33, Pages 14154-14159Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004958
Keywords
C-H alkylation; electrosynthesis; homogeneous catalysis; nickel; redox-neutral reactions
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Funding
- DFG (Gottfried-Wilhelm-Leibniz award)
- Alexander-von-Humboldt Foundation
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Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel-catalyzed C-H alkylations of unactivated 8-aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a mild base and a user-friendly electrochemical setup. This electrocatalyzed C-H alkylation displays high functional group tolerance and is applicable to both the primary and secondary alkylation. Based on detailed mechanistic studies, a nickel(II/III/I) catalytic manifold has been proposed.
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