Alkoxysilanes for C–C Coupling Reactions

Chemfiles Volume 3 Article 5

The use of silicon compounds as transmetalation reagents has attracted much attention as a viable alternative to the popular Stille and Suzuki coupling reactions mainly due to the formation of nontoxic byproducts and stability to many reaction conditions.1-4 Silicon-based coupling reactions can be carried out using aryl-, heteroaryl-, or alkenyl- halides and alkoxysilanes in the presence of palladium or rhodium catalysts. Among the various types of silicon compounds available, alkoxysilanes are more effective in coupling reactions.5-11

Silicon-based coupling scheme

Figure 1.Silicon-based coupling scheme

Recently, considerable attention has been paid to the rhodiumcatalyzed addition of aryl(trialkoxy)silanes to carbonyl compounds, such as aldehydes, α,β-unsaturated ketones and esters.12

Rhodium catalyzed scheme

Figure 2.Rhodium catalyzed scheme



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