Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids
- 1 November 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (23) , 8024-8030
- https://doi.org/10.1021/jo9707848
Abstract
The cross-coupling reaction of arylboronic acid with chloroarenes to give biaryls was carried out in high yields at 70−80 °C in the presence of a nickel(0) catalyst and K3PO4 (3 equiv) in dioxane or benzene. The nickel(0) catalyst in situ prepared from NiCl2·L (L = dppf, 2PPh3) (3−10 mol %) and 4 equiv of BuLi at room temperature was recognized to be most effective. The reaction can be applicable to a wide range of chloroarenes having an electron-withdrawing or an electron-donating group such as 4-NC, 4-CHO, 2- or 4-CO2Me, 4-COMe, 4-NHAc, 4-Me, 4-OMe, 4-NH2, and 4-NMe2. The Hammett's plot of the substituent effect of chloroarenes revealed that the reaction involves a rate-determining oxidative addition of chloroarenes to the nickel(0) complex.Keywords
This publication has 22 references indexed in Scilit:
- Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes: Highly Effective Methods for Arylation or Alkenylation of Aryl ChloridesThe Journal of Organic Chemistry, 1996
- Palladium-catalyzed coupling of alkenyl iodonium salts with olefins: a mild and stereoselective Heck-type reaction using hypervalent iodineJournal of the American Chemical Society, 1991
- Chelate-assisted, palladium-catalyzed efficient carbonylation of aryl chloridesJournal of the American Chemical Society, 1989
- First Syntheses of Furo[2,3-C]Quinolines Through Pd(0)-Catalyzed Coupling of Furanboronic Acid with Functionalized HaloarenesSynthetic Communications, 1989
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986
- Palladium- or nickel-catalyzed cross coupling. A new selective method for carbon-carbon bond formationAccounts of Chemical Research, 1982
- Photochemical oxidation and rearrangement of dibenzobarrelene and dehydrojanuseneJournal of the American Chemical Society, 1979
- Decomposition of phenolic peresters. II. tert-Butyl 3,5-di-tert-butyl-2-hydroxyperbenzoate and tert-butyl 5-methyl 3-tert-butyl-2-hydroxyperbenzoateJournal of the American Chemical Society, 1975
- Evidence for the participation of aspartic acid-194 in a new acylation-deacylation reaction of .alpha.-chymotrypsinJournal of the American Chemical Society, 1972
- Electrophilic Displacement Reactions. XI. Solvent Isotope Effects in the Protodeboronation of Areneboronic Acids1-3Journal of the American Chemical Society, 1961