Neutral, Metal-free Hydration of Alkynes Using Microwave Irradiation in ­Superheated Water

Abstract

A novel methodology for the hydration of alkynes in superheated water using microwave irradiation is reported. Extension of this methodology to hydroamination of alkynes is also described.

microwave - alkynes - hydration - superheated water

References

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Commercial vendors of microwave instrumentation specifically for synthetic chemistry purposes include CEM (www.cem.com), Milestone (www.milestonesci.com) and Personal Chemistry (www.personalchemistry.com).

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19a

Typical Procedure for the Hydration of Alkynes: A suspension of the alkyne in a mixture of the alkyne (0.1 mol) and 3 mL water in a sealed reaction vial was heated at 200 °C in an Emrys^® synthesizer for 20 min, following which the sample was cooled using compressed air. The product usually separated from the water on standing or could be extracted using 3 mL diethyl ether to afford the desired ketones in yields described in Table [2] , which demonstrated purity and analytical data consistent with commercial products.

19b

Typical Procedure for the Hydroamination of Alkynes: A mixture of the alkyne (0.87 mmol), amine (0.87 mmol) and water (3 mL) in a sealed reaction vial was heated at 200 °C in an Emrys^® synthesizer for 20 min, following which the sample was cooled using compressed air. The product was extracted using diethyl ether (3 mL) to afford 0.23 g of 12 (ref. 17).