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Updated: Oct 27, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ni-Catalyzed Asymmetric Hydrophosphination of Unactivated Alkynes
Xu-Teng Liu1, Xue-Yu Han1, Yue Wu1
1Department of Chemistry, University of Science and Technology of China, Hefei 230026, People's Republic of China.
Abstract:
The practical synthesis of P-stereogenic tertiary phosphines, which have wide applications in asymmetric catalysis, materials, and pharmaceutical chemistry, represents a significant challenge. A regio- and enantioselective hydrophosphination using cheap and ubiquitous alkynes catalyzed by a nickel complex was designed, in which the toxic and air-sensitive secondary phosphines were prepared in situ from bench-stable secondary phosphine oxides. This methodology has been demonstrated with unprecedented substrate scope and functional group compatibility to afford electronically and structurally diversified P(III) compounds. The products could be easily converted into various precursors of bidentate ligands and organocatalysts, as well as a variety of transition-metal complexes containing both P- and metal-stereogenic centers.
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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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