Cross-coupling reactions of phenylmagnesium halides with fluoroazines and fluorodiazines.
The first nickel-catalyzed cross-coupling reactions between fluoroarenes and aryl organometallics using commercially available ligands are described. The nickel-catalyzed cross-coupling reactions between aryl Grignard reagents and fluoroazines and -diazines occurred in THF at room temperature using commercially available 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, or 1,1'-bis(diphenylphosphino)ferrocene as ligand. Various fluoro substrates such as pyridines, diazines (pyrazine, pyridazine), benzodiazines (quinoxaline), and quinolines were successfully involved in the reaction with phenylmagnesium halides (phenylmagnesium chloride, 2-methoxyphenylmagnesium bromide, and 4-methoxyphenylmagnesium bromide). The conditions used also allowed the cross-coupling of 4-fluorotoluene with arylmagnesium reagents.
Mongin
Florence
F
Laboratoire de Chimie Organique Fine et Hétérocyclique, IRCOF, UMR 6014, Place E. Blondel, BP 08, 76131 Mont-Saint-Aignan Cédex, France.
Mojovic
Ljubica
L
Guillamet
Benoît
B
Trécourt
François
F
Quéguiner
Guy
G