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Gold(I)-catalyzed intramolecular hydroamination of alkyne with trichloroacetimidates

Ji-Eun Kang1, Hak-Beom Kim, Jin-Woo Lee

  • 1Department of Chemistry, Hanyang University, 17 Haengdang-dong, Seongdong-gu, Seoul 133-791, Korea.

Organic Letters
|July 28, 2006
PubMed

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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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