Syntheses of 2-silicon-substituted 1,3-dienes

•Three different synthetic routes to 2-silyl substituted 1,3-dienes are presented.•Hydrosilylation of enynes yields mixtures of regioisomers.•Grignard chemistry is the best synthetic route when 2-halo-1,3-dienes are available.

A number of 2-silicon substituted 1,3-dienes have been prepared by one of three routes: 1) Reactions of 1,3-dienyl Grignard reagents with silyl electrophiles or silyl Grignard reagents with 1,3-dienyl electrophiles; 2) Hydrosilylation of enynes; 3) Enyne cross metathesis. The strengths and limitations of each preparative method are discussed.

Graphical abstractA number of 1,3-dienes have been prepared by: 1) Reactions of 1,3-dienyl Grignard reagents with silyl electrophiles or silyl Grignard reagents with 1,3-dienyl electrophiles; 2) Hydrosilylation of enynes; or 3) Enyne cross metathesis. Use of Grignard chemistry where possible is preferred over enyne hydrosilyation or cross metathesis.Figure optionsDownload full-size imageDownload as PowerPoint slide