Alkene Vinyl Silane

The process tolerates a wide range of alkenes including vinyl ethers silanes and sulfides as well as electronically unbiased terminal and internal alkenes.

Alkene vinyl silane.

Six years later the generation of 2 iodoethyl trimethylsilane from vinylsilane and hi was observed. 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. Vinyl silanes offer a regio and stereoselective route to alkenes.

This two step process leads to the anti markovnikov hydration of alkenes. Johnson synlett 2011 2811 2814. 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. The resultant n alkylphthalimides can readily be transformed to the corresponding primary amines.

Adducts from the trichlorosilane reactions can be oxidised to afford alcohols in moderate yields. A copper catalzed functionalization of propiolate esters with various grignard reagents in presence of trimethylsilyl trifluoromethanesulfonate enables the synthesis of substituted e vinyl silanes in good yields and excellent diastereoselectivities via a catalytic carbocupration silicon group migration sequence. The stereochemistry of the vinyl silane is important because this exchange usually occurs with retention of geometry as well.