Synfacts 2008(3): 0300-0300  
DOI: 10.1055/s-2008-1042732
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

ortho-Selective Cross-Coupling of Dichlorobenzenes with Grignard Reagents

Contributor(s): Paul Knochel, Andrei Gavryushin
S. Ishikawa, K. Manabe*
RIKEN, Wako, Japan
Further Information

Publication History

Publication Date:
21 February 2008 (online)


The problem of the regioselectivity in cross-coupling reactions of functionalized di­haloarenes is important from the practical point of view. In this publication, the authors demonstrated highly ortho-selective coupling reactions of dichlorinated phenols, anilines and their derivatives, bearing an anionic coordinating group. Aryl, hetaryl, and alkenylmagnesium halides are suitable coupling partners. Using a specially designed ligand 1, o-chlorine can be coupled preferentially in the presence of a bromine atom in another position.