Synlett 2000; 2000(12): 1801-1803
DOI: 10.1055/s-2000-8672
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A Mild and Efficient Protocol for the Catalytic Silylation of Aryl Bromides

Lukas J. Gooßen* , Abdel-Rahman S. Ferwanah
  • *Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany; Fax +49-208-306-2985; E-mail: goossen@mpi-muelheim.mpg.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

New catalyst systems were developed which facilitate palladium-catalyzed silylation of various functionalized aryl and heteroaryl bromides with hexamethyldisilane under unprecedented mild conditions. The use of two different sets of ligands and bases for electron-rich and electron-poor substrates, respectively, is crucial for achieving excellent product selectivities at 100 °C and atmospheric pressure. For electron-rich substrates, diphenyl-2′-pyridylphosphine in combination with K2CO3 gives the best results, whereas for electron-poor substrates, 2-(di-t-butylphosphino)biphenyl/KF is preferred. Even base-sensitive arylsilanes, which are inaccessible by the traditional routes via organolithium species or Grignard reagents, can be prepared in a single step and high yields.