Alkenyl- and Aryl[2-(hydroxymethyl)phenyl]dimethylsilanes:  An Entry to Tetraorganosilicon Reagents for the Silicon-Based Cross-Coupling Reaction

Abstract

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue.