The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides

A palladium/norbornene-catalyzed ortho-silylmethylation reaction using of (iodomethyl)cyclohexyloxydimethylsilane as the electrophile was reported. The ((cyclohexyloxy)dimethylsilyl)methyl group was readily oxidized using the Fleming-Tamao process or by ceric ammonium nitrate to give benzylic alcohol derivatives. This method was successfully applied in a concise synthesis of a biaryl analogue of schisandrins.