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Synthesis 1979; 1979(10): 761-786
DOI: 10.1055/s-1979-28829
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Electrophilic Substitution of Organosilicon Compounds- Applications to Organic Synthesis

T. H. Chan* , Ian Fleming
  • *Department of Chemistry, McGill University, Montreal, Canada
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Publication Date:
14 May 2002 (online)

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Electrophilic substitution of aryl, vinyl, alkynyl, and cyclopropyl groups can often be controlled by the presence of a silyl group in the starting material: the silyl group usually encourages attack at whichever site will generate a curbocationic centre ß to the silicon atom, and it is usually the silyl group which is lost in the second step of the reaction. This review describes both the synthesis of the silicon-containing substrates and the scope and limitations of their reactions with electrophiles. 1. Introduction 2. Arylsilanes 3. Vinylsilanes 4. Alkynylsilanes 5. Allylsilanes 6. Benzylsilanes 7. Homoallylsilanes 8. Cyclopropylsilanes 9. Cyclopropylcarbinylsilanes 10. Alkylsilanes 11. Conclusions