Synlett 2000; 2000(12): 1801-1803
DOI: 10.1055/s-2000-8672
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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.

    >