Nickel-catalyzed cross-coupling of aryl fluorides and organozinc reagents

J Org Chem. 2014 May 16;79(10):4285-92. doi: 10.1021/jo500619f. Epub 2014 Apr 25.

Abstract

Ni(PCy3)2Cl2 was demonstrated to effectively catalyze cross-coupling of aryl fluorides and organozinc reagents. Both electron-poor and -rich aryl fluorides can react effectively with nucleophiles including aryl-, methyl-, and benzylzinc chlorides. A wide range of substituents and functional groups are tolerated. In the presence of a directing group, PhC(O), the reaction is selective for cleavage of the C-F bond ortho to the carbonyl substituent in a difluoroarene.