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Hydroalkylation of alkynyl ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence

Igor Dias Jurberg1, Yann Odabachian, Fabien Gagosz

  • 1Département de Chimie, UMR 7652, CNRS/Ecole Polytechnique, 91128 Palaiseau, France.

Journal of the American Chemical Society
|February 18, 2010
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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