Palladium-catalyzed silylation of electron-deficient aryl iodides using triorganosilane in the presence of pyridine and LiCl

Palladium-catalysed silylation of aryl iodides with electron-withdrawing groups was efficiently achieved using pyridine and lithium chloride as additives and conducting the reaction at room temperature. Functionalized aryl[2-(hydroxymethyl)-phenyl]dimethylsilanes were also prepared by palladium-catalysed reaction using THP-protected [2-(hydroxymethyl)-phenyl] dimethylsilane as a silylating agent followed by deprotection. Rhodium-catalysed 1,4-addition of the arylsilane was carried out using cyclohexenone as an enone in excellent yield.