title: Copper-catalyzed 1,2-addition of α-carbonyl iodides to alkynes.
abstract: β,γ-Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β-γ-unsaturated ketones through 1,2-addition of α-carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)-trichostatin A, a histone deacetylase inhibitor.
authors.affiliation: Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISCI-LSCI, BCH 3305, 1015 Lausanne (Switzerland) http://lsci.epfl.ch.
authors.forename: Tao
authors.initials: T
authors.lastname: Xu
authors.forename: Xile
authors.initials: X
authors.lastname: Hu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D056572:Histone Deacetylase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D006877:Hydroxamic Acids / Q000138:chemical synthesis / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002254:Carbonates; D056572:Histone Deacetylase Inhibitors; D006877:Hydroxamic Acids; D007454:Iodides; D007659:Ketones; D008698:Mesylates; D002586:Cesium; C012589:trichostatin A; D003300:Copper; C012077:trifluoromethanesulfonic acid; C545311:cesium carbonate
keywords: 1,2-addition reactions; alkynes; copper; ketones; olefination