Biaryl synthesis using highly stable aryl[2-(hydroxymethyl)phenyl]dimethylsilanes and aryl iodides under fluoride-free conditions

Abstract

Readily accessible and highly stable aryl[2-(hydroxymethyl)phenyl]dimethylsilanes cross-couple with various aryl iodides under mild reaction conditions employing K2CO3 as a base at 50 °C. Use of CuI as a co-catalyst is essential for the success of the present coupling reaction, which tolerates a diverse range of functional groups to afford a wide variety of biaryl products. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinated silicates having a transferable aryl group at an axial position and facilitate transmetalation from silicon to copper and then to palladium. © 2006 NIMS and Elsevier Ltd.