ArticleAngewandte Chemie (International ed. in English)2022
Selective Cross-Ketonization of Carboxylic Acids Enabled by Metallaphotoredox Catalysis.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Article
- Synthesis of C4-Acyl Glycosides by Cross-Ketonization: The Importance of Precise Temperature Control in Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- The Golden Age of Thermally Activated Delayed Fluorescence Materials: Design and Exploitation.Chemical reviews · 2024Review
- Synthesis of Stereodefined Enones from the Cross-Electrophile Coupling of Activated Acrylic Acids with Alkyl Bromides.Organic letters · 2024Article
- Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins.Beilstein journal of organic chemistry · 2023Article
- Selective Cross-Ketonization of Carboxylic Acids Enabled by Metallaphotoredox Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
2 authors.
Funding
Abstract
Carboxylic acids are attractive building blocks for synthetic chemistry because they are chemically stable, abundant, and commercially available with substantial structural diversity. The process of combining two carboxylic acids to furnish a ketone is termed ketonization. This is a potentially valuable transformation that has been underutilized in organic synthesis due to the harsh reaction conditions generally required and the lack of selectivity obtained when coupling two distinct carboxylic acids. We report herein a metallaphotoredox strategy that selectively generates unsymmetrical ketones via cross-ketonization of two structurally dissimilar carboxylic acids. Cross-selectivity is achieved by exploiting divergent reactivity of differentially substituted acids towards critical one- and two-electron processes in the proposed coupling mechanism. This method is broadly applicable to a variety of functionalized carboxylic acids. It can also be applied to acids of similar steric profile by exploiting differences in their relative rates of decarboxylation.
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