Synfacts 2006(8): 0833-0833  
DOI: 10.1055/s-2006-941999
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Regioselective Halogenation of Arenes

Contributor(s): Paul Knochel, Andrei Gavryushin
D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford*
University of Michigan, Ann Arbor, USA
Further Information

Publication History

Publication Date:
21 July 2006 (online)

Significance

This work describes a novel catalytic method for the regioselective halogenation of a variety of substituted arenes, bearing an ortho-directing group. Chlorination, bromination and iodination of arenes is possible, using 5 mol% of Pd(OAc)2 as a catalyst and readily available N-halosuccinimides as halogenating agents. A large number of directing groups are suitable for the reaction. This method is often complementary to the usual electrophilic halogenation, and allows a straightforward preparation of various aryl halides, which are otherwise difficult to achieve.