Highly Regioselective Remote Lithiation of Functionalized 1,3‐bis‐Silylated Arenes

Substituted arenes flanked by two bulky triethylsilyl groups are regiospecifically lithiated in 5‐position with nBuLi•PMDTA at 25 °C. The resulting aryllithiums reacted with a broad range of electrophiles such as ketones, isocyanates, Weinreb‐amides, allyl bromides or CO2 at 25 °C. These bis‐silylated arenes were converted in simple reaction sequences to silyl‐free tetrasubstituted arenes. This remote lithiation was extended to 2,6‐bis(triethylsilyl)pyridine as well as a 3,3'‐bis(triethylsilyl)biphenyl.

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