FeCl3-Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes
- 13 November 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (25), 9838-9841
- https://doi.org/10.1021/jo701782g
Abstract
[Graphics] An efficient FeCl3-catalyzed substitution reaction of propargylic acetates with enoxysilanes under mild conditions to afford corresponding gamma-alkynyl ketones has been developed. The substitution reaction is followed by a TsOH-catalyzed cyclization without purification of the gamma-alkynyl ketone intermediates, offering a straightforward synthetic route to tri- or tetrasubstituted furansKeywords
This publication has 21 references indexed in Scilit:
- Ruthenium‐Catalyzed Propargylic Substitution Reactions of Propargylic Alcohols with Oxygen‐, Nitrogen‐, and Phosphorus‐Centered NucleophilesChemistry – A European Journal, 2005
- Rhenium-Catalyzed Aromatic PropargylationOrganic Letters, 2004
- Rhenium-Catalyzed Coupling of Propargyl Alcohols and Allyl SilanesJournal of the American Chemical Society, 2003
- A Mild C−O Bond Formation Catalyzed by a Rhenium-Oxo ComplexJournal of the American Chemical Society, 2003
- Propargylation of Aromatic Compounds with Propargylic Alcohols Catalyzed by a Cationic Diruthenium ComplexAngewandte Chemie, 2003
- Ruthenium-Catalyzed Propargylic Substitution Reaction of Propargylic Alcohols with Thiols: A General Synthetic Route to Propargylic SulfidesJournal of the American Chemical Society, 2002
- Ruthenium-Catalyzed Propargylation of Aromatic Compounds with Propargylic AlcoholsJournal of the American Chemical Society, 2002
- Ruthenium-Catalyzed Cycloaddition of Propargylic Alcohols with Phenol Derivatives via Allenylidene Intermediates: Catalytic Use of the Allenylidene Ligand as the C3 UnitJournal of the American Chemical Society, 2002
- Novel Propargylic Substitution Reactions Catalyzed by Thiolate-Bridged Diruthenium Complexes via Allenylidene IntermediatesJournal of the American Chemical Society, 2000
- Synthetic applications of transition-metal-stabilized carbenium ions. Selective alkylation of ketones and ketone derivatives with (propargyl)dicobalt hexacarbonyl cationsJournal of the American Chemical Society, 1980