title: Fully substituted pyranones via quasi-heterogeneous genuinely ligand-free Migita-Stille coupling of iodoacrylates.
abstract: Migita-Stille coupling of (Z)-β-iodoacrylates with (E)-α-stannyl allylic alcohols to furnish 5-alkylidene-4-substituted-5,6-dihydro-2H-pyran-2-ones is efficiently catalyzed by 2% Pd black in DMF, while Pd(PPh3)4 is inactive. Heterogeneous Pd released in solution is most likely responsible for the catalysis. The reaction is applicable to other substrates, without having to resort to ligands, additives, and/or solid support for Pd. The resulting pyranones can be rearranged to fully functionalized pyranones in another single step.
authors.affiliation: Department of Inorganic and Organic Chemistry and ‡Department of Analytical Chemistry, Faculty of Pharmacy, Charles University in Prague , Akademika Heyrovského 1203, Hradec Králové 500 05, Czech Republic.
authors.forename: Jiří
authors.initials: J
authors.lastname: Kratochvíl
authors.forename: Zdeněk
authors.initials: Z
authors.lastname: Novák
authors.forename: Mukund
authors.initials: M
authors.lastname: Ghavre
authors.forename: Lucie
authors.initials: L
authors.lastname: Nováková
authors.forename: Aleš
authors.initials: A
authors.lastname: Růžička
authors.forename: Jiří
authors.initials: J
authors.lastname: Kuneš
authors.forename: Milan
authors.initials: M
authors.lastname: Pour
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000179:Acrylates; D006847:Hydrocarbons, Iodinated; D011714:Pyrans; D010165:Palladium