Aerobic Oxidation of Aldehydes to Carboxylic Acids
Summary
Aerobic oxidation of aldehydes to carboxylic acids represents a cornerstone transformation in both academic and industrial chemistry, enabling the sustainable production of value-added acids from readily available substrates. By employing molecular oxygen as the terminal oxidant, these processes minimise hazardous by-products and align with principles of green chemistry. Mechanistically, the reaction may proceed via radical-chain pathways, organocatalytic cycles or metal-mediated redox cycles, each harnessing oxygen under mild temperatures and pressures. The choice of catalyst and reaction medium governs selectivity, rate and substrate scope, allowing tailored syntheses of aliphatic and aromatic acids. Such methodologies hold global significance in fine-chemicals manufacture, agrochemicals, pharmaceuticals and polymer precursors, offering improved atom economy, lower energy consumption and reduced waste compared to classical stoichiometric oxidants.
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Aerobic Oxidation of Aldehydes to Carboxylic Acids publication trend
The graph below shows the total number of articles in aerobic oxidation of aldehydes to carboxylic acids across all publications each year (not limited to Nature Index journals).
Technical terms
Aerobic oxidation: Oxidation process employing molecular oxygen as the oxidant under ambient or mild conditions to convert organic substrates into more oxidised products.
Aldehyde: An organic functional group characterised by a carbonyl centre bonded to at least one hydrogen atom, general formula R–CHO, prone to oxidation.
Carboxylic acid: Organic compounds containing the –COOH group, widely used as intermediates and end-products in pharmaceuticals, polymers and agrochemicals.
N-heterocyclic carbene (NHC): A stable, divalent carbon species within a heterocyclic framework that serves as an organocatalyst to activate substrates towards nucleophilic and oxidative transformations.
N-hydroxyphthalimide (NHPI): A redox mediator capable of generating phthalimide N-oxyl radicals under aerobic conditions, promoting selective hydrogen-atom abstraction in radical-chain oxidations.
References
- NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes. Beilstein Journal of Organic Chemistry (2013).
- Solvent Effect on Product Distribution in the Aerobic Autoxidation of 2-Ethylhexanal: Critical Role of Polarity. Frontiers in Chemistry (2022).
- Efficient Synthesis of 2-Ethylhexanoic Acid via N-Hydroxyphthalimide Catalyzed Oxidation of 2-Ethylhexanal with Oxygen. Materials (2023).
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