Synfacts 2007(12): 1296-1296  
DOI: 10.1055/s-2007-991326
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Silylation of Aryl Chlorides with Hexamethyldisilane

Contributor(s): Paul Knochel, Andrei Gavryushin
E. McNeill, T. E. Barder, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
22 November 2007 (online)

Significance

Aryl silanes are highly useful intermediates in the synthesis of functionalized arenes due to the ability of the silyl group to direct the attack of an electrophile to the ipso position. Herein, an excellently general and convenient method for the preparation of aryl silanes from the corresponding chlorides is reported. The synthetic utility of the new silylation reaction was demonstrated by the one-pot conversion of several aryl chlorides into the corresponding aryl iodides.