Catalytic Hydration of Alkynes in Organic Synthesis

The catalytic hydration of alkynes represents a cornerstone transformation in organic chemistry, enabling the direct conversion of carbon–carbon triple bonds into carbonyl functionalities under mild conditions. Traditionally mediated by mercuric salts or precious‐metal complexes, contemporary research has shifted towards more sustainable and selective catalysts, including non‐toxic main‐group metals, heterogeneous solid acids and photoactivated clusters. Key challenges include control of regioselectivity (Markovnikov versus anti‐Markovnikov addition), compatibility with aqueous media and catalyst recyclability. Advances in homogeneous and heterogeneous catalysis have broadened substrate scope to both terminal and internal alkynes, while continuous‐flow technologies and benign reaction media improve safety, scalability and environmental footprint. The reaction finds application in fine‐chemical synthesis, pharmaceutical intermediates and isotope‐labelling protocols, underscoring its global significance and versatility.

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Catalytic Hydration of Alkynes in Organic Synthesis publication trend

The graph below shows the total number of articles in catalytic hydration of alkynes in organic synthesis across all publications each year (not limited to Nature Index journals).

Technical terms

Catalytic hydration: Addition of water across an alkyne’s triple bond in the presence of a catalyst to form a carbonyl compound.

Markovnikov addition: Regioselective addition where the hydrogen atom attaches to the carbon with more hydrogens, yielding the more substituted carbonyl product.

Solid acid catalyst: A heterogeneous acid catalyst with immobilised acidic sites on a solid support, facilitating reactions in aqueous or solvent-free systems.

Continuous flow processing: A reactor format in which reagents flow continuously through a fixed catalyst bed or coil, offering improved safety, scalability and heat management.

Ionic liquid: A molten salt at ambient temperature, comprising bulky organic cations and inorganic or organic anions, used as a non-volatile, recyclable reaction medium.

References

1. Facile Photochemical/Thermal Assisted Hydration of Alkynes Catalysed under Aqueous Media by a Chalcogen Stabilized, Robust, Economical, and Reusable Fe3Se2(CO)9 Cluster. Organics (2023).
2. 1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF3: the case of alkyne hydration. Chemistry vs electrochemistry. Beilstein Journal of Organic Chemistry (2023).
3. Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions. Molecules (2021).