ArticleOrganic letters2020
Nickel-Catalyzed Conversion of Amides to Carboxylic Acids.
Article in Organic letters, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 27 citations in OpenAlex.
- Organocatalytic Synthesis of Amides Using Thioacids and Anilines via Electron Donor-Acceptor Photoactivation.The Journal of organic chemistry · 2026Article
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Enantioselective nickel-catalyzed Mizoroki-Heck cyclizations of amide electrophiles.Chemical science · 2024Article
- Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling.SynOpen (2017) · 2023Article
- Mechanochemical Defluorinative Arylation of Trifluoroacetamides: An Entry to Aromatic Amides.The Journal of organic chemistry · 2023Article
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (International ed. in English) · 2022Review
- Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.ACS catalysis · 2020Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
We report the conversion of amides to carboxylic acids using nonprecious metal catalysis. The methodology strategically employs a nickel-catalyzed esterification using 2-(trimethylsilyl)ethanol, followed by a fluoride-mediated deprotection in a single-pot operation. This approach circumvents catalyst poisoning observed in attempts to directly hydrolyze amides using nickel catalysis. The selectivity and mildness of this transformation are shown through competition experiments and the net-hydrolysis of a complex valine-derived substrate. This strategy addresses a limitation in the field with regard to functional groups accessible from amides using transition metal-catalyzed C-N bond activation and should prove useful in synthetic applications.
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Registered trials
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