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P. 34-37 /

Si–B bond activation in asymmetric Cu(I) and Rh(I) catalysis

EDUARD HARTMANN, MARTIN OESTREICH*
*Corresponding authorInstitut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany

Abstract

Heterolytic cleavage of the Si–B bond through transmetalationwith (chiral) Cu–O or Rh–O complexes produces syntheticallyuseful silicon nucleophiles that participate in several typicalC–Si bond-forming reactions. Conjugate addition proceedswith superb levels of enantiocontrol employing either Cu(I)–carbene or Rh(I)–phosphine complexes, and an asymmetriciminium ion catalysis merged with an achiral Cu(I)-catalysedSi–B bond activation is now also known. The Cu(I) catalysis isan attractive alternative entry into the established chemistryof silicon-based cuprates and displays considerable scope,as further exemplified by regioselective allylic substitutionand addition reactions.