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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)