Arylation and Vinylation Reactions of Benzo[b]furan via Organopalladium Intermediates
- 1 April 1973
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 46 (4) , 1220-1225
- https://doi.org/10.1246/bcsj.46.1220
Abstract
The Heck reaction of benzo[b]furan with arylpalladium chloride leads to the formation of 2-arylbenzo[b]-furan derivatives. In the presence of palladium acetate, benzo[b]furan reacts in benzene to give 2,2′-bibenzo[b]furyl, accompanied by 2-arylbenzo[b]furan. In the phenylation of [2-2H]benzo[b]furan with phenylpalladium salts, it was confirmed that no hydride shift takes place in the reaction. In the presence of palladium acetate, benzo[b]furan also reacts with olefin to produce benzo[b]furyl-substituted olefins, accompanied by a small amount of 2,2′-bibenzo[b]furyl, and from the reaction of [β,β-2H2]styrene and benzo[b]furan in the presence of palladium acetate it was confirmed that no hydride shift occurs in the reaction.This publication has 6 references indexed in Scilit:
- Aromatic substitution of olefins. VI. Arylation of olefins with palladium(II) acetateJournal of the American Chemical Society, 1969
- Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivativesJournal of the American Chemical Society, 1968
- The Acid-Catalyzed Hydration of StyreneJournal of the American Chemical Society, 1966
- The oxidative coupling of aromatic compounds with palladium saltsRecueil des Travaux Chimiques des Pays-Bas, 1965
- Studies of Benzofurans as Potential Antimicrobial Agents. II. Synthesis of β‐(2‐Benzofuryl)‐Acrylic Acid and its DerivativesJournal of the Chinese Chemical Society, 1961
- The Mechanism of Aromatic Mercuration.1 I. Orientation EffectsJournal of the American Chemical Society, 1950