Microwave-Promoted and Chelation-Controlled Double Arylations of Terminal Olefinic Carbon of Vinyl Ethers
- 9 April 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (10) , 3345-3349
- https://doi.org/10.1021/jo035815f
Abstract
Herein we report a rapid, palladium-catalyzed terminal diarylation of the chelating olefin N,N-dimethyl(2-ethenyloxy)ethanamine under noninert conditions utilizing controlled microwave heating as a convenient energy source. Among the aryl bromides examined, both electron-rich and electron-poor substrates were demonstrated to furnish useful yields after only 10-120 min of directed microwave heating at 160-200 degrees C. The good terminal regioselectivity suggests that the precatalyst (Herrmann's palladacycle) serves as a source of weakly coordinated palladium(0) in the investigated high-temperature Heck process.Keywords
This publication has 16 references indexed in Scilit:
- Chloropalladated Propargyl Amine: A Highly Efficient Phosphine-Free Catalyst Precursor for the Heck ReactionOrganic Letters, 2003
- Transition Metal Catalysis and Microwave Flash Heating in Organic ChemistryPublished by Wiley ,2002
- Intermolecular Heck Reaction: Scope, Mechanism, and Other Fundamental Aspects of the Intermolecular Heck ReactionPublished by Wiley ,2002
- Advances in the Heck chemistry of aryl bromides and chloridesTetrahedron, 2001
- A Novel Borosilicate Cage Compound with an Incomplete B4Si4 Cube Structure: [(tBuSi)4(CH2=CHC6H4B)4O10]Published by Wiley ,2000
- [Bis(2-pyridyldimethylsilyl)methyl]lithium. New Reagent for the Stereoselective Synthesis of VinylsilanesOrganic Letters, 2000
- Application of palladacycles in Heck type reactionsJournal of Organometallic Chemistry, 1999
- Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl HalidesChemistry – A European Journal, 1997
- Effects of High Pressure on the Heck Reaction. Is It Possible to Control Dehydropalladation of Alkylpalladium Intermediates Having β-Hydrogens?Tetrahedron Letters, 1995
- Chelation-controlled, palladium-catalyzed arylation of enol ethers with aryl triflates. Ligand control of selection for α-or β-arylation of [2-(dimethylamino)ethoxy]ethene.Tetrahedron, 1994