Rhenium-Catalyzed Aromatic Propargylation
- 12 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (8) , 1325-1327
- https://doi.org/10.1021/ol049649p
Abstract
A mild aromatic propargylation reaction, employing an air- and moisture-tolerant rhenium−oxo complex ((dppm)ReOCl3) as a catalyst and a propargyl alcohol as the electrophile, is described. The reaction tolerates a broad range of functional groups and regioselectively affords propargylic arenas without formation of the isomeric allenyl adducts. The potential of this rhenium(V)-catalyzed reaction is exemplified by application of the propargylation to the synthesis of O-methyldetrol, mimosifoliol, and β-apopicropodophyllin.Keywords
This publication has 19 references indexed in Scilit:
- Rhenium-Catalyzed Coupling of Propargyl Alcohols and Allyl SilanesJournal of the American Chemical Society, 2003
- Kinetic and Thermodynamic Barriers to Carbon and Oxygen Alkylation of Phenol and Phenoxide Ion by the 1-(4-Methoxyphenyl)ethyl CarbocationJournal of the American Chemical Society, 2003
- Facile One-Pot Synthesis of Photochromic PyransOrganic Letters, 2003
- Catalytic Methods for C-H Bond Functionalization: Application in Organic SynthesisAdvanced Synthesis & Catalysis, 2003
- Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalizationTetrahedron, 2003
- A Mild C−O Bond Formation Catalyzed by a Rhenium-Oxo ComplexJournal of the American Chemical Society, 2003
- Ruthenium-Catalyzed Propargylation of Aromatic Compounds with Propargylic AlcoholsJournal of the American Chemical Society, 2002
- Rare-Earth Metal Triflates in Organic SynthesisChemical Reviews, 2002
- Two New Aromatic Constituents from the Rootwood of Aeschynomene mimosifoliaJournal of Natural Products, 1996
- Stable carbonium ions. CXI. Styryl(1-phenylethyl) cation and substituted styryl cationsJournal of the American Chemical Society, 1971