Related Experiment Video
Updated: Dec 16, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Pd-Catalyzed Cyanoselenylation of Internal Alkynes: Access to Tetrasubstituted Selenoenol Ethers
Abstract:
The intra- and intermolecular synthesis of selenium-substituted acyclic and heterocyclic acrylonitrile derivatives is presented. The 1,2-difunctionalization of several internal alkynes substituted not only by aliphatic and aromatic residues but also by heteroelements is realized by the Pd-catalyzed activation of aromatic and aliphatic selenocyanates. A high functional group tolerance allows straightforward access to a broad scope of tetrasubstituted olefins. X-ray studies of some products reveal noncovalent chalcogen-chalcogen interactions between oxygen and selenium.
Related Concept Videos
02:24Reduction 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.
02:17Reduction 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...
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
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.
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
02:26Preparation and Reactions of Sulfides
01:26Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction