Alkene Vinyl Silane

0 0 vinyl silanes react with electrophiles in a highly regioselective process in which the silicon is replaced by the electrophile at the ipso carbon atom.

Alkene vinyl silane.

Johnson synlett 2011 2811 2814. An intermolecular anti markovnikov hydroamination of alkenes has been developed using triethyl phosphite and n hydroxyphthalimide. Terminal vinyl silanes heck coupling non alkyl si substituents are required to activate the vinyl silane to heck cross coupling subsequent functionalisation of the silyl diene alkoxysilanes generally require forcing conditions and even then react only in poor yields with significant protodesilylated products recovered. Six years later the generation of 2 iodoethyl trimethylsilane from vinylsilane and hi was observed.

The resultant n alkylphthalimides can readily be transformed to the corresponding primary amines. In 1948 it was discovered that allyltrimethylsilane reacts with hydrobromic acid to give 2 bromopropyl trimethylsilane. This two step process leads to the anti markovnikov hydration of alkenes. Adducts from the trichlorosilane reactions can be oxidised to afford alcohols in moderate yields.

The stereochemistry of the vinyl silane is important because this exchange usually occurs with retention of geometry as well. The process tolerates a wide range of alkenes including vinyl ethers silanes and sulfides as well as electronically unbiased terminal and internal alkenes. Gaseous and flammable silanes are inconvenient to use in chemical reactions.