Pd-Catalyzed C-H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group.

An efficient Pd-catalyzed ortho-C-H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C-H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.