Vinyl silanes offer a regio- and stereoselective route to alkenes

Vinyl silanes react with electrophiles in a highly regioselective process in which the silicon is replaced by the electrophile at the ipso carbon atom. The stereochemistry of the vinyl silane is important because this exchange usually occurs with retention of geometry as well.

CLICK the examples below to see how E- and Z-vinyl silanes react:

E-vinyl silane

Z-vinyl silane

I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97, 2063–2192.



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