Palladium-Catalyzed Intramolecular Oxidative Alkylation of Unactivated Olefins
- 20 December 2002
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (3) , 648-649
- https://doi.org/10.1021/ja026317b
Abstract
Reaction of 5,5-dimethyl-8-nonene-2,4-dione catalyzed by PdCl2(CH3CN)2 (5 mol %) in the presence of CuCl2 (2.5 equiv) at room temperature for 3 h formed 2-acetyl-3,6,6-trimethyl-2-cyclohexenone in 96% isolated yield. Palladium-catalyzed intramolecular oxidative alkylation tolerated a range of substitution and was applicable to the synthesis of spirobicyclic compounds and to the cyclization of zeta-alkenyl beta-keto esters.Keywords
This publication has 17 references indexed in Scilit:
- Cobalt-Catalyzed Heck-Type Reaction of Alkyl Halides with StyrenesJournal of the American Chemical Society, 2002
- Fine Feathers Make Fine Birds: The Heck Reaction in Modern GarbAngewandte Chemie International Edition in English, 1995
- Palladium(II)-catalysed oxidation of allylic amines with molecular oxygenJournal of the Chemical Society, Chemical Communications, 1994
- New aspects of oxypalladation of alkenesAccounts of Chemical Research, 1990
- Transition Metals in the Synthesis and Functionalization of Indoles [New Synthesis Methods (72)]Angewandte Chemie International Edition in English, 1988
- Urea as the most reactive and versatile nitrogen nucleophile for the palladium(2+)-catalyzed cyclization of unsaturated aminesJournal of the American Chemical Society, 1988
- Lewis acid-induced nucleophilic substitution reactions of .beta.-nitro sulfides via episulfonium ionsThe Journal of Organic Chemistry, 1987
- Synthetic Applications of the Palladium-Catalyzed Oxidation of Olefins to KetonesSynthesis, 1984
- Palladium-assisted carboacylation of olefinsJournal of the American Chemical Society, 1980
- The Oxidation of Olefins with Palladium Chloride CatalystsAngewandte Chemie International Edition in English, 1962