Related Experiment Video
Updated: Jul 11, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Gold-catalyzed hydroamination/cycloisomerization reaction of 1,6-enynes
Lucie Leseurre1, Patrick Yves Toullec, Jean-Pierre Genêt
1Laboratoire de Synthèse Sélective Organique et Produits Naturels, E.N.S.C.P., UMR 7573, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
Abstract:
An efficient Au(I) catalytic system is described for the hydroamination/cycloisomerization reaction of functionalized 1,6-enynes. The reaction leads to carbo- and heterocyclic amino derivatives in good to excellent yields. The cyclizations were conducted in the presence of PPh(3)AuCl/AgSbF(6) catalyst in THF or dioxane at room temperature. The use of allyloxycarbonyl carbamate has allowed the formation of free amino derivatives via sequential Au- and Pd-catalyzed reactions.
More Related Videos
06:46Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide